- Volume
-
v. 84 ISBN 9780470099018
Description
Organic Syntheses: Volume 84 continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas.
- Volume
-
v. 85 ISBN 9780470432273
Description
The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.
- Volume
-
v. 86 ISBN 9780470556146
Description
The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.
Table of Contents
Preparation of (3,5-Dimethoxy-1-Phenyl Cyclohexa-2,5-Dienyl)-Acetonitrile Through Birch Reductive Alkylation (BRA) (Raphael Lebeuf, Muriel Berlande, Frederic Robert, and Yannick Landais). Synthesis of Tert-Butyl (1S,2S)-2-Methyl-3-Oxo-1-Phenylpropylcarbamate By Asymmetric Mannich Reaction (Jung Woon Yang, Subhas Chandra, Pan, and Benjamin List).
Synthesis of Pyrazolo[1,5-a]Pyridines Via Azirines: Preparation of 2-(3-Bromophenyl)-6-(Trifluoromethyl)Pyrazolo[1,5-a]Pyridine (Stephen Greszler and Kirk L. Stevens).
Benzyl Alcohol as an Alkylating Agent Using the Ruthenium-Catalyzed Borrowing Hydrogen Strategy (Tracy D. Nixon, Paul A. Slatford, Michael K. Whittlesey and Jonathan M. J. Williams).
2-(2,2-Dibromoethenyl)-Benzenamine (Christopher Bryan, Valentina Aurregi and Mark Lautens).
(S)-(-)-2-Allylcyclohexanone (Manfred Braun, Panos Meletis, and Mesut Fidan).
Preparation of 4-Spirocyclohexyloxazolidinone By C-H Bond Nitrene Insertion (Kim Huard and Helene Lebel).
Preparation of (S)-4-Isopropyl-N-Propanoyl-1,3-Thiazolidine-2-Thione (Erik Galvez, Pedro Romea, and Felix Urpi).
Stereoselective Synthesis of Anti -Methyl-ss-Methoxy Carboxylic Compounds (Erik Galvez, Pedro Romea, and Felix Urpi).
Synthesis of 2-Arylindole-4-Carboxylic Amides: [2-(4-Fluorophenyl)-1H-Indol-4-YL]-1-Pyrrolidinylmethanone (Jeffrey T. Kuethe and Gregory L. Beutner).
Palladium (II) Acetate-Butyldi-1- Adamantylphosphine Catalyzed Arylation of Electron-Rich Heterocycles. Preparation of 5-Phenyl-2-Isobutylthiazole (Anna Lazareva, Hendrich A. Chiong, and Olafs Daugulis).
Mild and Efficient One-Pot Curtius Rearrangement: Preparatino of N-Tert-Butyl Adamantanyl-1-YL-Carbamate (Olivier Leogane and Helene Lebel).
Enantioselective Oxidation of An Alkyl Aryl Sulfide: Synthesis of (S)-(-) Methyl p-Bromophenyl Sulfoxide (Carmelo Drago, Emma-Hane Walker, Lorenzo Caggiano and Richard F. W. Jackson).
Protection of Diols with 4-(tert-Butyldimethylsilyloxy)Benzylidene Acetal and Its Deprotection:(4-((4R,5R)-4,5-Diphenyl-1,3-Dioxolan-2-YL) Phenoxy) (Tert-Butyl)Dimethylsilane (Hiroyuki Osajima, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama, and Tohru Fukuyama).
Synthesis of 2-[3,3'-DI-(Tert-Butoxycarbonyl)-Aminodipropylamine]-4,6,-Dichloro-1,3,5-[Tris-Piperazine]-Triazine As a Core for the Large Scale Syntehsis of Melamine (Triazine) Dendrimers (Abdellatif Chouai, Vincent J. Venditto, and Eric E. Simanek).
Large Scale, Green Syntehsis of a Generation-1 Melamine (Triazine) Dendrimer) (Abdellatif Chouai, Vincent J. Venditto, and Eric E. Simanek).
The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-Acetylphenyl) Acetate (David C. Ebner, Uttam K. Tambar, and Brian M. Stoltz).
Convenient Preparation of 3-Ethoxycarbonyl Benzofurans From Salicylaldehydes adn Ethyl Diazoacetate (Matthew E. Dudley, M. Monzur Morshed, and M. Mahmun Hossain).
Preparation of (S)-Tert-Butylphon (Michael R. Krout, Justin T. Mohr, and Brian M. Stoltz).
Preparation of (S)-2-Allyl-2-Methylcyclohexanone (Justin T. Mohr, Michael R. Krout, and Brian M. Stoltz).
Phosphine-Catalyzed [4+2] Annulation: Synthesis of Ethyl 6-Phenyl-1-Tosyl-1,2,5,6-Tetrahydropyridine-3-Carboxylate (Kui Lu and Ohyun Kwon).
Syntehsis of Polyynes by In Situ Desilylative Brominatino and Palladium-Catalyzed Coupling: (7-(Benzyloxy)Hepta-1,3,5-Triynyl) Triisopropylsilane (Soonho Hwang, Hee Ryong Kang, and Sanghee Kim).
Enantioselective Preparation of Dihydropyrimidones (Jennifer M. Goss, Peng Dai, Sha Lou, and Scott E. Schaus).
One-Pot Multicomponent Preparation of Tetrahydropyrzaoloquinolinones and Tetrahydropyrazoloquinazolinones (Toma N. Glasnov and C. Oliver Kape).
(3R,7aS)-3-(Trichloromethyl)Tetrahydropyrrolo[1,2-C]Oxazol-1(3H)-One: An Air and Moisture Stable Reagent For the Synthesis of Optically Active -Branched Prolines (Gareld D. Artmann III, Ryan J. Rafferty, and Rovert M. Williams).
Vinylation with Inexpensive Silicon-Based Reagents: Preparation of 3-Vinylquinoline and 4-Vinylbenzophenone (Scott E. Denmark and Christophe R. Butler).
Low Pressure Carbonylation of Epoxides to ss-Lactones (John W. Kramer, Daniel S. Treitler, and Geoffrey W. Coates).
Tetrakis(Dimethylamino)Allene (Alois Furstner, Manuel Alcarazo, and Helga Krause).
Efficient One-Pot Synthesis of Bis(4-Tert-Butylphenyl)Iodonium Triflate (Marcin Bielawski and Berit Olofsson).
Pd(0)-Catalyzed Diamination of Trans-1-Phenyl-1,3-Butadiene with Di-Tert-butyldiaziridinone As Nitrogen Source (Haifeng Du, Baoguo Zhao, and Yian Shi).
Synthesis of Ethyl 2-Ethanoyl-2-Methyl-3-Phenylbut-3-Enoate (Taisuke Fujimoto, Kohei Endo, Masaharu Nakamura, and Eiichi Nakamura).
Synthesis of 4,5-Dimethyl-1,3-Dithiol-2-One (Perumalreddy Chandreasekaran and James P. Donahue).
B-Protected Haloboronic Acids For Iterative Cross-Coupling (Steven G. Ballmer, Eric P. Gillis, and Martin D. Burke).
Rhodium-Catalyzed Enantioselective Addition of Arylboronic Acids to In Situ Generated N-Boc Arylimines. Preparatin of (S)-Tert-Butyl (4-Chlorophenyl) (Thiophen-2-YL)Methylcarbamate (Morten Storgaard and Jonathan A. Ellman).
Magnesiation of Weakly Activated Arenes Using tmp2Mg 2LiC1:Synthesis of Tert-Butyl Ethyl Phthalate (Christoph J. Rohbogner, Andreas J. Wagner, Giuliano C. Clososki, and Paul Knochel).
ERRATA.
1,4-BIS(Trimethylsilyl)Buta-1,3-Diyne (Graham E. Jones, David A. Kendrick, and Andrew B. Holmes).
- Volume
-
v. 73 ISBN 9780471147015
Description
Consists of a series of 28 checked and edited procedures that describe in detail the preparation of generally useful synthetic reagents, intermediates or products or exemplify important new synthetic methods of expected broad applicability and significances. Chemoselective and stereoselective general synthetic techniques, optimized preparations of reagents currently not available commercially and preparation of enantiomerically pure materials beginning with readily available enantiomerically pure natural substances are among the topics covered.
Table of Contents
Partial table of contents:
3-[(1S)-1,2-Dihydroxyethyl]-1,5-Dihydro-3H-2,4-Benzo-Dioxepine (R. Oi & K. Sharpless).
(4R)-(+)-tert-Butyldimethylsiloxy-2-Cyclopenten-1-One (L. Paquette, et al.).
(4S)-(-)-tert-Butyldimenthylsiloxy-2-Cyclopenten-1-One (L. Paquette & T. Heidelbaugh).
Alkylidenation of Ester Carbonyl Groups: (Z)-1-Ethoxy-1-Phenyl-1-Hexene (K. Takai, et al.).
4-Dodecylbenzenesulfonyl Azides (G. Hazen, et al.).
Bis(Trifluoroethyl) (Carbo-Ethoxymethyl) Phosphonate (C. Patois, et al.).
Diethyl (2S,3R)-2-(N-tert-Butoxy-Carbonyl)Amino-3-Hydroxy Succinate (S. Saito, et al.).
4-Ketoundecanoic Acid (M. Tschantz, et al.).
1,3,5-Cyclooctatriene (M. Oda, et al.).
3-Pyrroline (A. Meyers, et al.).
2-Cyclohexene-1,4-Dione (M. Oda, et al.).
4,5-Dibenzoyl-1,3-Dithiole-1-Thione (T. Hansen, et al.).
Indexes.
- Volume
-
v. 74 ISBN 9780471156567
Description
This book offers a series of twenty-eight checked and edited procedures that describe in detail the preparation of generally useful synthetic reagents, intermediates, and heterocycles. It also includes new synthetic methodology on the leading edge of organic chemistry.
Table of Contents
Partial table of contents:
(-)-2-0-Benzyl-L-Glyceraldehyde and Ethyl(R,E)-4-0-Benzyl-4,5-Dihydroxy-2-Pentenoate (B. Steuer, etal.).
Bis(Trimethylsilyl) Peroxide (BTMSPO) (P. Dembech, et al.).
Synthesis of Epoxides Using Dimethyldioxirane: trans-Stilbene Oxide(R. Murray & M. Singh).
Phenyl Vinyl Sulfide (D. Reno & R. Pariza).
Regio- and Stereoselective Carboxylation of Allylic BariumReagents: (E)-4,8- Di-Methyl-3,7-Nonadienoic Acid (A. Yanagisawa,et al.).
Preparation of 3-Bromopropiolic Esters: Methyl and tert-Butyl3-Bromopropiolates (J. Leroy).
Regioselective Synthesis of 3-Substituted Indoles: 3-Ethylindole(M. Amat, et al.).
Indexes.
- Volume
-
v. 75 ISBN 9780471183723
Description
Volume 75 of the Organic Synthesis series contains 29 carefully checked and edited experimental procedures describing leading-edge synthetic methods, important reagents, and useful building blocks.
Table of Contents
Partial table of contents:
Catalytic Asymmetric Allylation Reactions:(S)-1-Phenylmethoxy)-4-Penten-2-OL (G. Keck & D.Krishnamurthy).
Ethyl (R)-2-Azidopropionate (A. Thompson, et al.).
(4R,5S)-4,5-Diphenyl-3-Vinyl-2-Oxazolidinone (T. Akiba, etal.).
3-Chloro-2-(Chloromethyl)-1-Propene (K. Lynch & W.Dailey)
[1.1.1]Propellane (K. Lynch & W. Dailey).
N-Benzyl-2,3-Azetidinedione (C. Behrens & L. Paquette).
Preparation of Cyanoalkynes: 3-Phenyl-2-Propynenitrile (F.-T. Luo,et al.).
2-Trimethylsilylethane-Sulfonyl Chloride (SES-Cl) (S. Weinreb, etal.).
4-Dimethylamino-N-Triphenyl-Methylpyridinium Chloride (A. Bhatia,et al.).
6,7-Dihydrocyclopenta-1,3-Dioxin-5(4H)-One (K. Chen, et al.).
3-Cyclopentene-1-Carboxylic Acid (J.-P. Depres & A.Greene).
Unchecked Procedures.
Indexes.
- Volume
-
v. 78 ISBN 9780471235804
Description
The Organic Syntheses series presents protocols for the synthesis of useful chemical compounds; for each protocol, safety warnings are included along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are also detailed, along with the source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers. Volume 78 in the series provides twenty-nine carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. The procedures in Volume 78 fall into four general areas:
reagents and methods for catalytic asymmetric synthesis
organometallic chemistry, ligands, and transformations of organometallic reagents
synthetically useful reagents and intermediates
useful synthetic transformations.
- Volume
-
v. 71 ISBN 9780471305316
Description
Consists of 30 checked and edited experimental procedures that illustrate new synthetic techniques or describe the preparation of particularly useful chemicals. Features procedures exemplifying important methods for preparing enantiomerically pure substances by asymmetric catalysis; details a reliable zirconium-based process for the coupling of alkynes and enones; concludes with the preparation of four useful starting materials. A section on waste disposal information is included.
Table of Contents
Partial table of contents:
Asymmetric Hydrogenation of 3-OXO Carboxylates Using BinaprutheniumComplexes: (R)-(-)-Methyl 3-Hydroxybutanoate (M. Kitamura, etal.).
Direct Degradation of the Biopolymer Poly [(R)-3-HydroxybutyricAcid] to (R)-3-Hydroxybutanoic Acid and Its Methyl Ester (D.Seebach, et al.).
3-(S)-[(tert-Butyldiphenylsilyl)-Oxy]-2-Butanone (L. Overman &G. Rishton).
Schwartz's Reagent (S. Buchwald, et al.).
4-Methoxy-4'-Nitrobiphenyl (J. Stille, et al.).
Ubiquinone-1 (Y. Naruta & K. Maruyama).
Benzoannelation of Ketones: 3,4-Cyclododeceno-1-Methylbenzene (M.Tius & G. Kannangara).
2-Methylene-1, 3-Dithiolane (K. Dahnke & L. Paquette).
Methoxycarbonylmethylation of Aldehydes Via Siloxycyclopropanes:Methyl 3,3-Dimethyl-4-Oxobutanoate (H.-U.
Reissig, et al.).
9-Bromo-9-Phenylfluorene (T. Jamison, et al.).
Indexes.
- Volume
-
v. 72 ISBN 9780471307273
Description
A collection of synthetic methods, reagents and compounds appearing at the leading edge of organic chemical research. This volume contains 32 checked and edited procedures addressing some of the most significant new techniques and chemical entities to emerge in recent years. Commences with nine procedures whose principle affinity lies in the use of naturally derived starting materials to produce important chiral intermediates in enantiomerically pure form. Four methods are based on current advances in catalysis; three provide useful synthetic intermediates; eight procedures highlight practical developments in organometallic chemistry; organic fluorine compounds and methods for their preparation are covered in four procedures; and processes for four important organophosphorus and organosulfur compounds conclude the volume.
Table of Contents
Partial table of contents:
L-(S)-Glyceraldehyde Acetonide (C. Hubschwerlen & J.-L.
Specklin).
D-(R)-Glyceraldehyde Acetonide (C. Schmid & J. Bryant).
(R)-(+)-2-Hydroxy-1,2,2-Triphenylethyl Acetate (M. Braun, etal.).
(1R,5R)-(+)-Verbenone of High Optical Purity (M. Sivik, etal.).
Benzocyclobutenone by Flash Vacuum Pyrolysis (P. Schiess, etal.).
An Efficient Synthesis of Indole-2-Acetic Acid Methyl Esters (S.Modi, et al.).
7-Methoxyphthalide (X. Wang, et al.).
Phenylthioacetylene (P. Magriotis & J. Brown).
Warning.
Unchecked Procedures.
Indexes.
- Volume
-
v. 76 ISBN 9780471348863
Description
The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.
Table of Contents
Partial table of contents:
Resolution of 1,1'-Bl-2-Naphthol (D. Cai, et al.).
1S-(-)-1,3-Dithiane 1-Oxide (P. Page, et al.).
(1S, 2R)-1-Aminoindan-2-OL (J. Larrow, et al.).
Methyl (S)-2-Phthalimido-4-Oxobutanoate (P. Meffre, et al.).
(tert-Butyldimethylsilyl)Allen (A. Myers & B. Zheng).
6-Chloro-1-Hexene and 8-Chloro-1-Octene (P. Mazerolles, et al.).
2-Chlorophenyl Phosphorodi-Chloridothioate (V. Ravikumar & B. Ross).
9,10-Diphenylphenanthrene (G. Olah, et al.).
Unchecked Procedures.
Indexes.
- Volume
-
v. 77 ISBN 9780471395676
Description
Organic Syntheses, Volume 77 describes twenty-eight checked and edited experimental procedures, spanning a broad range of synthetic methodologies, and provides chemists with a compendium of new or little known experimental procedures which lead to useful compounds or that illustrate important new developments in methodology. For every procedure, safety warnings are presented along with detailed descriptions for the preparation, purification, and identification of the compound in question. Additionally, special reaction conditions are detailed, along with the source of reagents, helpful waste disposal guidelines, discussions of results, references to the primary literature, and an appendix of nomenclature and registry numbers. Coverage is divided into four main sections devoted to: reagents and procedures for asymmetric synthesis; chemical processes; chemical reagents; and chemical compounds, respectively.
Table of Contents
Partial table of contents:Preparation of (R,R)-1,2:4,5-Diepoxypentane (S. Rychnovsky, et al.).
Synthesis and Diastereoselective Alkylation of Pseudoephedrine Amides (A. Myers & B. Yang).
(R)-(+)-2-Hydroxy-1,2,2-Triphenylethyl Acetate (J. Macor, et al.).
Synthesis of 1,1-Dimethylethyl (S)-4-Formyl-2,2-Dimethyl-3-Oxazolidinecarboxylate By Reduction of the Alcohol (A. Dondoni & D. Perrone).
Synthesis of (S,E)-1-(Methoxymethoxy)-1-Tributylstannyl-2-Butene (J. Marshall, et al.).
Allylindation in Aqueous Media: Methyl 3-(Hydroxymethyl)-4-Methyl-2-Methylenepentanoate (G. Bennett & L. Paquette).
The Synthesis of 2-Alkyl-4-Pyrones From Meldrum's Acid (M. Crimmins, et al.).
9-Ethyl-3,6-Dimethylcarbazole (DMECZ) (J. Buck, et al.).
Bis(Pinacolato)Diboron (T. Ishiyama, et al.).
-Tosylbenzyl Isocyanide (J. Sisko, et al.).
Methyl 2,3-O-(6,6'-Octahydro-6,6'-Bi-2H-Pyran-2,2'-Diyl)--D-Galactopyranoside (S. Ley & H. Osborn).
Cyclopropylacetylene (E. Corley, et al.).
3-Nitropropanal, 3-Nitropropanol, and 3-Nitropropanal Dimethyl Acetal (H. Griesser, et al.).
Cyclopropene: A New Synthesis and Its Diels-Alder Reaction with Cyclopentadiene (P. Binger, et al.).
Unchecked Procedures.
Indexes.
- Volume
-
v. 79 ISBN 9780471415305
Description
The Organic Syntheses series presents protocols for the synthesis of useful chemical compounds. For each protocol, safety warnings are included along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are also detailed, along with the source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers. Volume 79 in the series provides thirty carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. The procedures in Volume 79 fall into four general areas:
reagents and methods for catalytic asymmetric synthesis
organometallic chemistry, ligands, and transformations of organometallic reagents
synthetically useful reagents and intermediates
useful synthetic transformations
- Volume
-
v. 80 ISBN 9780471445319
Description
Organic Syntheses consists of protocols for the synthesis of useful chemical com-pounds. For each protocol, safety warnings are presented along with detailed experimental de-scriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are also detailed, along with the source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers.
Table of Contents
Collective Vol. I A revised edition of Annual Volumes I-IX 580
Collective Vol. II A revised edition of Annual Volumes X-XIX 654
Collective Vol. III A revised edition of Annual Volumes 20-29 890
Collective Vol. IV A revised edition of Annual Volumes 30-39 1036
Collective Vol. V A revised edition of Annual Volumes 40-49 1234
Cumulative Indices to Collective Volumes, I, II, III, IV, V
Collective Vol. VI A revised edition of Annual Volumes 50-59 1208
Collective Vol. VII A revised edition of Annual Volumes 60-64 602
Collective Vol. VIII A revised edition of Annual Volumes 65-69 696
Collective Vol. IX A revised edition of Annual Volumes 70-74 840
- Volume
-
v. 82 ISBN 9780471682561
Description
Reflecting the increased pace of research and the many recent advances in organic chemistry, the Organic Syntheses series serves as a single source compendium of the most up-to-date procedures in use. Organic Syntheses consists of protocols for the synthesis of useful chemical compounds. For each protocol, safety warnings are presented along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are detailed, along with the source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers.
Table of Contents
Preparation of 1,4:5,8-Dimethano-1,2,3,4,5,6,7,8-Octahydro-9,10-Dimethaoxyanthracenium Hexachiloroantimonate(4+Sbcl6-): A Highly Robust Radical-Cation Salt. Preparation of Optically Active (R,R)-Hydrobenzoin From Benxoin or Benzil.
2,2-Diethoxy-1-Isoxyanoethane.
Preparation of (S,S) -1,2--BIS(tert-Butylmethylphosphino)-Ethane ((S,S)-t-Bu-BISP) As a Rhodium Complex.
Preparation of Hexakis(4-Bromophenyl)Benzene (HBB).
An Efficient, Highly Diastereo- And Enantioselective Hetero-Diels-Alder Catalyst. Preparation of (2S, 6R)-6-(tert-Butyldimethylsilyloxymethyl)-2-Methoxy-2,5-Diyhdropyran.
Lipase-Catalyzed Resolution of 4-Trimethylsilyl-3-Butyn-2-OL and Conversion of the (R)-Enantiomer To (R)-3-Butyn-2-Yl Mesylate and ({)-1-tributylstannyl-1,2-Butadiene.
Iridium-Catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate.
1-(tert-Butyliminomethyl)-1,3-Dimethylurea Hydrochloride.
Ortho-Formylation of Phenols: Preparation of 3-Bromosalicylaldehyde.
Preparation of 1-Methoxy-2-(4-Methoxyphenoxy)Benzene.
D-Ribonolactone and 2,3-Isopropylidene-(D-Ribonolactone)
Preparation of 4-Acetylamino-2,2,6,6-Tetramethyl-Piperidine-1-Oxoammonium Tetrafluoroborate, and the Oxidation of Geraniol to Geranial.
(2S)-(-)-3exo-(Morpholino)Isoborneol [(-)-MIB].
Conversion of Arylalkylketones Into Dichloroalkenes: 1-Chloro-4-(2,2-Dichloro-1-Methylvinyl)Benzene.
1,4,-Dioxene.
(R)-(+)-3,4-Dimethylcyclohex-2-EN-1-One.
A Practical and Safe Preparation of 3,5-BIS-(Trifluoromethyl)Acetophenone.
Asymmetric Alcoholysis of Meso-Anhydrides Mediated By Alkaloids.
Iridium-Catalyzed C-HBorylation of Arenes and Heteroarenes: 1-Chloro-3-Iodo-5-(4,4,5,5-Tetramethyl-1,3,2,-Dioxaborolan-2-YL)Benzene and 2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-YL)Indole.
Asymmetric Rearrangement of Allylic Trichloroacetimidates: Preparation of (s)-2,2,2-Trichloro-N-(1-Propylallyl)Acetamide.
Preparation of (Triphenylphosphoranylidene)-Ketene From (Methoxycarbonylmethylene)-Triphenylphosphorane.
Preparation of [1-(Methoxymethylcarbamoyl)-Aethyl]Phosphonic Acid BIS(2,2,2-Trifluoroethyl)Ester: A Useful Intermediate in the Synthesis of Z-Unsaturated N-Methoxy-N-Methylamides.
(Rs)-(+)-2-Methyl-2-Propanesulfinamide.
Preparation of 1-Butyl-3-Methylimidazolium Tetrafluoroborate.
Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation reaction.
Alkyne via Solid-Liquid Phase-Transfer Catalyzed Dehydrohalogenation: Acetylene Dicarboxaldehyde Tetramethyl Acetal and Acetylene Dicarboxaldeyde Dimethyl Acetal.
Catalytic reduction of Amides to Amines with Hydrosilanes Using a Tributhenium Carbonyl Cluster as the Catalyst.
- Volume
-
v. 81 ISBN 9780471682578
Description
Reflecting the increased pace of research and the many recent advances in organic chemistry, this series serves as a single-source compendium of the most up-to-date and significant procedures currently in use.
- Volume
-
v. 83 ISBN 9780471979876
Description
Organic Syntheses consists of protocols for the synthesis of useful chemical compounds. Each protocol is repeated in the laboratory of one of the editorial board members for accuracy or for missing experimental details prior to publication. For each reaction, source of reagents, waste disposal information, a discussion of the results, references to the primary literature, and an appendix of nomenclature and registry numbers are discussed. Volume 83 continues the tradition of providing significant and interesting procedures, which will prove worthwhile to many synthetic chemists working in increasingly diverse areas.
- Volume
-
v. 87 ISBN 9781118005149
Description
Organic syntheses consists of protocols for the synthesis of useful chemical compounds. Organic Syntheses, Volume 87 provides carefully checked and edited experimental protocols that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. For each protocol, safety warnings are presented along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are also detailed. This current volume continues the tradition of providing significant and interesting procedures for synthetic chemists working in increasingly diverse areas.
Table of Contents
Metal-Free One-Pot Oxidative Amination of Aromatic Aldehydes: Conversion of Benzaldehyde to N-Benzoyl Pyrrolidine 1
Kekeli Ekoue-Kovi and Christian Wolf
A Practical and Scalable Synthesis of N-Halo Compounds: 2-Chloro-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline 8
Yong-Li Zhong and Paul G. Bulger
Regioselective C-4 Bromination of Oxazoles: 4-Bromo-5-(Thiophen-2-YL) Oxazole 16
Bryan Li, Richard A. Buzon, and Zhijun Zhang
Synthesis of Spiroborate Esters from 1,2-Aminoalcohols, Ethylene Glycol and Triisopropyl Borate: Preparation of (S)-1-(1,3,2-Dioxaborolan-2-Yloxy)-3-Methyl-1,1-Diphenylbutan-2-Amine 26
Viatcheslav Stepanenko, Kun Huang and Margarita Ortiz-Marciales
Catalytic Enantioselective Borane Reduction of Benzyl Oximes: Preparation of (S)-1-Pyridin-3-YL-Ethylamine BIS Hydrochloride 36
Kun Huang and Margarita Ortiz-Marciales
Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation 53
Naohiro Kirai and Yoshihiko Yamamoto
Preparation of (S)-3,3'-BIS-Morpholinomethyl-5,5',6,6',7,7',8,8'-Octahydro-1,1'-BI-2-Naphthol 59
Mark Turlington and Lin Pu
Catalytic Asymmetric Addition of an In-Situ Prepared Arylzinc to Cyclohexanecarboxaldehyde: (R)-(+)- -Cyclohexyl-3-Methoxy-Benzenemethanol 68
Albert M. DeBerardinis, Mark Turlington, and Lin Pu
Microwave-Assisted Synthesis of 1,3-Dimesitylimidazolinium Chloride 77
Morgan Hans and Lionel Delaude
Synthesis of (3-Chlorobutyl)Benzene by the Cobalt-Catalyzed Hydrochlorination of 4-Phenyl-1-Butene 88
Boris Gaspar, Jerome Waser, and Erick M. Carreira
Synthesis of Substituted Indazoles via (3+2) Cycloaddition of Benzyne and Diazo Compounds 95
Feng Shi and Richard C. Larock
Palladium-Catalyzed Cross-Coupling Using an Air-Stable Trimethylaluminum Source. Preparation of Ethyl 4-Methylbenzoate 104
Andrej Vinogradov and Simon Woodward
Synthesis of Dimethyl 2-Phenycyclopropane-1,1-Dicarboxylate Using an Iodonium Ylide Derived from Dimethyl Malonate 115
Sebastien R. Goudreau, David Marcoux and Andre B. Charette
New, Convenient Route for Trifluoromethylation of Steroidal Molecules 126
Xiang-Shu Fei, Wei-Sheng Tian, Kai Ding, Yun Wang and Qing-Yun Chen
Preparation of Ethyl 1-Benzyl-4-Fluoropiperidine-4-Carboxylate 137
Jianshe Kong, Tao Meng, Pauline Ting, and Jesse Wong
Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to ,ss-Unsaturated Esters: Asymmetric Synthesis of (S)-ss-Leucine 143
Stephen G. Davies, Ai M. Fletcher, and Paul M. Roberts
Cyclohexene Imine (7-Aza-Bicyclo[4.1.0]Heptane) 161
Iain D. G. Watson, Nicholas Afagh and Andrei K. Yudin
Preparation of (E)-(2-Iodovinyl)Benzene From Benzyl Bromide and Diiodomethane 170
James A. Bull, James J. Mousseau and Andre B. Charette
Synthesis of Tetraorganosilanes: (Chloromethyl)Dimethylphenylsilane 178
Submitted by Kei Murakami, Hideki Yorimitsu, and Koichiro Oshima
A General Method for Copper-Catalyzed Arylation of Acidic Arene C-H Bonds. Preparation of 2-Chloro-5-(3-Methylphenyl)-Thiophene 184
Joseph Alvarado, Hien-Quang Do, and Olafs Daugulis
1,3,5-Triacetylbenzene 192
Peter J. Alaimo, Amanda-Lynn Marshall, David M. Andrews and Joseph M. Langenhan
Organocatalytic -Methylenation of Aldehydes: Preparation of 3,7-Dimethyl-2-Methylene-6-Octenal 201
Meryem Benohoud, Anniina Erkkila, and Petri M. Pihko
Ruthenium-Catalyzed Arylation of Ortho C-H Bond in an Aromatic with an Arylboronate: 8-Phenyl-1-Tetralone 209
Kentaroh Kitazawa, Takuya Kochi, and Fumitoshi Kakiuchi
Amide Formation by Decarboxylative Condensation of Hydroxylamines and -Ketoacids: N-[(1S)-1 Phenylethyl]-Benzeneacetamide 218
Lei Ju and Jeffrey W. Bode
One-Pot Diazotization and Heck Reaction of Methyl Anthranilate: 2-(3-Oxopropyl) Benzoic Acid Methyl Ester 226
Florencio Zaragoza
Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-Alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-Phenylethynyl)-N-(Phenylmethyl)Benzenesulfonamide 231
Alexis Coste, Francois Couty and Gwilherm Evano
Direct Fluorination of the Carbonyl Group of Benzophenones Using Deoxo-Fluor (R): Preparation of BIS(4-Fluorophenyl) Difluoromethane 245
Ying Chang, Hyelee Lee, Chulsung Bae
Preparation and [2+2] Cycloaddition of 1-Triisopropylsiloxy-1-Hexyne with Methyl Crotonate: 3-Butyl-4-Methyl-2-Triisopropylsiloxy-Cyclobut-2-Enecarboxylic Acid Methyl Ester 253
Valeriy Shubinets, Michael P. Schramm, and Sergey A. Kozmin
Pd(0)-Catalyzed Asymmetric Allylic and Homoallylic Diamination of 4-Phenyl-1-Butene with DI-Tert-Butyldiaziridinone 263
Baoguo Zhao, Haifeng Du, Renzhong Fu, and Yian Shi
Synthesis of Enamides from Ketones: Preparation of N-(3,4-Dihydronaphthalene-1-YL)Acetamide 275
Hang Zhao, Charles P. Vandenbossche, Stefan G. Koenig, Surendra P. Singh, and Roger P. Bakale
Safe and Scalable Preparation of Barluenga's Reagent 288
Justin M. Chalker, Amber L. Thompson, and Benjamin G. Davis
Palladium-Catalyzed Alkyl-Alkyl Suzuki Cross-Couplings of Primary Alkyl Bromides at Room Temperature: (13-Chlorotridecyloxy)Triethylsilane 299
Sha Lou and Gregory C. Fu
Synthesis of Chiral Pyridine Bis(Oxazoline) Ligands for Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary allylic Chlorides with Alkylzincs:2,6-BIS[(4R)-4,5-Dihydro-4-(2-Phenylethyl)-2-Oxazolyl]-Pyridine 310
Sha Lou and Gregory C. Fu
Nickel-Catalyzed Asymetric Negishi Cross-Couplings of Racemic Secondary Allylic Chlorides with Alkylzincs: (S,E)-Ethyl 6-(1,3-Dioxolan-2-YL)-4-Methylhex-2-Enoate 317
Sha Lou and Gregory C. Fu
Nickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary a-Bromo Amides with Alkylzinc Reagents: (s)-N-Benzyl-7-Cyano-2-Ethyl-N-Phenylheptanamide 330
Sha Lou and Gregory C. Fu
One-Pot Synthesis of 5H-Indazolo-[3,2-b] Benzo[d]-1,3-Oxazine: Two Efficient Preparative Methods 339
Danielle M. Solano, Jeffrey D. Butler, Makhluf J. Haddadin and Mark J. Kurth
Preparation of Chiral and Achiral Triazolium Salts: Carbene Precursors with Demonstrated Synthesis Utility 350
Harit U. Vora, Stephen P. Lathrop, Nathan T. Reynolds, Mark S. kerr, Javier Read de Alaniz, and Tomislav Rovis
Synthesis of A N-Mesityl Substituted Aminoindanol-Derived Triazolium Salt 362
Justin R. Struble and Jeffrey W. Bode
Preparation of O-Allyl-N-(9-Anthracenyl-Methyl)-Cinchonidium Bromide as a Phase Transfer Catalyst 377
E. J. Corey and Mark C. Noe
- Volume
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v. 88 ISBN 9781118173978
Description
The current volume continues the tradition of the Organic Synthesis series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including phar-maceuticals, fine chemicals, agrochemicals, and biotech.
Table of Contents
Editorial: Organic Syntheses: The "Gold Standard" for Experimental Synthetic Organic Chemistry 1
Rick L. Danheiser -Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(-Br)] 4
David S. Huang, Ryan J. DeLuca, and John F. Hartwig
The Preparation of Amides by Copper-medicated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 14
Maxime Giguere-Bisson, Woo-Jin Yoo, and Chao-Jun Li
Synthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 22
Louis-Charles Campeau and Keith Fagnou
The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Animation of 2-Aminophenyl Ketoximes 33
Carla M. Councellar, Chad C. Eichman, Brenda C. Wray, Eric R. Welin, and James P. Stambuli
The Preparation of (2R,5S)-2-t-Butyl-3,5-Dimethylimidazolidin-4-One 42
Thomas H. Graham, Benjamin D. Horning, and David W. C. MacMillan
Synthesis of Et2SB*SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 54
Scott A. Snyder and Daniel S. Treitler
Discussion Addendum for: Asymmetric Synthesis of (M)-2- Hydroxymethyl-1-(2-Hydroxy-3,6-Dimethylphenyl)Naphthalene via a Configurationally Unstable Biaryl Lactone 70
G. Bringmann, T. A. M. Gulder, and T. Gulder
Synthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 79
Yasunori Yamamoto, Juugaku Sigai, Miho Takizawa, and Norio Miyaura
Synthesis of (+)-B-Allyldiisopinocampheylborane and It Reaction with Aldehydes 87
Huikai Sun and William R. Roush
Discussion Addendum for: Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene 102
Scott E. Denmark and Jack Hung-Chang Liu
The Preparation of Cyclohept-4-Enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 109
Paul A. Wender, Adam B. Lesser, and Lauren E. Sirois
Organocatalytic Enantioselective Synthesis of Bicyclic ss-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 121
Henry Nguyen, Seongho Oh, Huda Henry-Riyad, Diana Sepulveda, and Daniel Romo
Phosphine-Catalyzed [3 + 2) Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 138
Ian P. Andrews and Ohyun Kwon
Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxy-Phosphinyl)Acetate 152
Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama
Discussion Addendum for: 5-ENDO-TRIG Cyclization of 1,1-Difluoro-1-Alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole (1H-Indole, 3-Butyl-2-Fluoro-1-[(4-Methylphenyl)Sulfonyl-) 162
Junji Ichikawa
Preparation of a Thrifluoromethyl Transfer Agent: 1-Trifloromethyl-1,3-Dihydro-3,3-Dimenthyl-1,2-Benziodoxole 168
Patrick Eisenberger, Iris Kieltsch, Raffael Koller, Kyrill Stanek, and Antonio Tongni
Synthesis of (S,S)-Diisopropyl Tartrate (E)-Crothylboronate and Its Reaction with Aldehydes: (2R,3R,4R)-1,2-Dideoxy-2-Ethenyl-4,5,-O-(1-Methylethylidene)-Xylitol 181
Huikai Sun and William R. Roush
Discussion Addendum for: 4-Methoxy-4'-Nitrophenyl. Recent Advances in the Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis 197
Robert M. Williams
Discussion Addendum for: Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene 202
Norio Miyaura
Discussion Addendum for: Palladium (0)-Catalyzed Reaction of 9-Alkyl-9-Borabicyclo[3.3.1]Nonane with 1-Bromo-1-Phenylthioethene: 4-(3-Cyclohexenyl )-2-Phenylthio-1-1-Butene 207
Norio Miyaura
Preparation of Isopropyl 2-Diazoacetyl(Phenyl)Carbamate 212
Hubert Muchalski, Amanda B. Doody, Timothy L. Troyer, and Jeffrey N. Johnson
Gram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-Bromopheneyl)Aziridine 2-Carboxylate 224
Aman A. Desai, Roberto Moran-Ramallal, and William D. Wulff
Cu-Catalyzed Azide-Alkyne Cycloaddition: Preparation of Tris((1-Benzyl-1H-1,2,3-Triazolyl )Methyl)Amine 238
Jason E. Hein, Larissa B. Krasnova, Masayuki Iwasaki, and Valery V. Fokin
Lithiated Primary Alkyl Carbamates for the Homologation of Boronic Esters
Matthew P. Webster, Benjamin M. Partridge, and Varinder K. Aggarwal
Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-Diene 260
Sandro Cacchi, Enrico Morera, and Giorgio Ortar
Discussion Addendum for: Synthesis of Indoles by Palladium-Catalyzed Reductive N-Heteroannulation of 2-Nitrostyrenes: Methyl Indole-4-Carboxylate 291
Bjoern C. Soederberg
An Economical Synthesis of 4-Trimethysilyl-2-Butyn-1-OL 296
Alexander N. Wein, Rongbiao Tong, and Frank E. McDonald
Silver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis of Allengic Sulfones 309
Michael Harmata, Zhengxin Cai and Chaofeng Huang
(Sa,S)-N-[2'-(Methylphenylsulfonamido)-1-1'-Binaphthyl-2-YL]Pyrrolidine-2-Carboxamide: An Organocatalyst for the Direct Aldol Reaction 317
Santiago F. Viozquez, Gabriela Guillene, Carmen Najera, Ben Bradshaw, Gorka Etxebarria-Jardi, and Josep Bonjoch
Synthesis of (S)-8a-Methyl-3,4,8,8a-Tetrahydro-1,6-(2H,7H)-Naphthalenedione via N-Tosyl-(Sa)-Binam-L-Pholinamide Organocatalysis 330
Ben Bradshaw, Gorka Etxebarria-Jardi, Josep Bonjoch, Santiago F. Viozquez, Gabriela Guillena, and Carmen Najera
Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes 342
Robert J. Ely and James P. Morken
Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-Oxo-5-Heptynyl)-1-3-Dithiane 353
Marilda P. Lisboa, Tunf T. Hoang, and Gregory B. Dudley
Synthesis and Diasteroselective Aldol Reactions of a Thiazolidinethione Chiral Auxiliary 364
Michael T. Crimmins, Hamish S. Christie, and Colin O. Hughes
Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes: 3-Methyl-2-(Trimethylsilyl)Indole 377
Yu Chen, Nataliya A. Markina, Tuanli Yao, and Richard C. Larock
An Intramolecular Amination of Aryyl Halides with a Combination of Copper (I) and Cesium Acetate: Preparation of 5,6-Dimethoxyindole-1,2-Dicarboxylic Acid 1-Benzyl Ester 2-Methyl Ester 388
Toshiharu Noji, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama
Ligand-Free Copper(II) Oxide Nanoparticles-Catalyzed Synthesis of Substituted Benzoxazoles 398
Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy
(R)-3,3'-Bis(9-Phenanthyryl)-1,1'-Binaphthalene-2,2'-Diyl Hydrogen Phosphate 406
Wenhao Hu, Jing Zhou, Xinfang Xu, Weijun Liu, and Liuzhu Gong
Enantioselective Three-Component Reaction for the Preparation of ss-Amino-a-Hydroxy Esters 418
Jing Zhou, Xinfang Xu, and Wenhao Hu
Mild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz's Reagent) 427
Matthew W. Leighty, Jared T. Spletstoser, and Gunda I. Georg
- Volume
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v. 89 ISBN 9781118743195
Description
The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.
- Volume
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v. 90 ISBN 9781118893845
Description
The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.
- Volume
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v. 91 ISBN 9781119054160
Description
The demand for synthetic procedures that can be duplicated may be less egregious today than in 1921, but there is still a need. To date, Organic Syntheses has filled this need with 90 volumes of "checked" experimentals; and with the culmination of Kay Brummond's term as a member of the editorial board, the addition of Volume 91.
Table of Contents
- Discussion Addendum: Resolution of 1,1'-Bi-2-Naphthol
- (R)-(+)- and (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(BINAP) 1
David L. Hughes Discussion Addendum for: Practical Synthesis of Novel Chiral Allenamides: (R)-4-Phenyl-3-(1,2-propadienyl)oxazoldin-2-one 12
Yong-Chua Teo and Richard P. Hsung
N-Carboxylated-2-substituted Indoles and 2,3-Disubstituted-2,3-dihydro-4-quinolones from 2-Alkynylbenzamides 27
Noriko Okamoto, Kei Takeda, and Reiko Yanada
Pd-Catalyzed External-CO-Free Carbonylation: Preparation of 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate 39
Hideyuki Konishi, Tsuyoshi Ueda, and Kei Manabe
Rhodium-Catalyzed Direct Amination of Arene C-H Bonds Using Azides as the Nitrogen Source 52
Sae Hume Park, Yoosu Park, and Sukbok Chang
Synthesis of Alkynyliodonium Salts: Preparation of Phenyl (phenylethynyl)iodonium Trifluoroacetate 60
Luke I. Dixon, Michael A. Carroll, George J. Ellames and Thomas J. Gregson
Palladium-catalyzed 1,4-Addition of Terminal Alkynes to Conjugated Enones 72
Feng Zhou, Liang Chen and Chao-Jun Li
Cross-Coupling of Alkenyl/Aryl Carboxylates with Grignard Reagents via Fe-Catalyzed C-O Bond Activation 83
Bi-Jie Li, Xi-Sha Zhang and Zhang-Jie Shi
Preparation of 5-Hydroxycyclopentenones Via Conjugate Addition-Initiated Nazarov Cyclization 93
Joshua L. Brooks, Yu-Wen Huang, and Alison J. Frontier
Synthesis of Arylboronic Pinacol Esters from Corresponding Arylamines 106
Di Qiu, He Meng, Liang Jin, Shengbo Tang, Shuai Wang, Fangyang Mo, Yan Zhang and Jianbo Wang
Preparation of Alkanesulfonyl Chlorides from S-Alkyl Isotghiourea Salts via N-Chlorosuccinimide Mediated Oxidative Chlorosulfonation 116
Zhanhui Yang and Jiaxi Xu
DABCO-bis(sulfur dioxide), DABSO, as an easy-to-handle source of SO2: Sulfonamide preparation 125
Edward J. Emmett and Michael C. Willis
One-pot Preparation of (S)-N-[(S)-1-Hydroxy-4-metghyl-1,1-diphenylpentan-2-yl]pyrrolidine-2-carboxamide from L-Proline 137
Wacharee Hamying, Nonognaphat Duangdee, and Albrecht Berkessel
Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Pentenyl Isocyanate and 4-Ethynylanisole: Preparation and Use of Taddol-pyrrolidine Phosphoramidite 150
Kevin M. Oberg, Timothy J. Martin, Mark Emil Oinen, Derek M. Dalton, Rebecca Keller Friedman, Jamie M. Neely, and Tomislav Rovis
Synthesis and Use of a Trifluoromethylated Azomethine Ylide Precursor: Ethyl 1-Benzyl-trans-5-(trifluoromethyl)pyrrolidine-3-carboxylate 162
Daniel M. Allwood, Duncan L. Browne and Steven V. Ley
Enantioselective Organocatalytic- -Arylation of Aldehydes 175
Pernille H. Poulsen, Mette Overgaard, Kim L. Jensen and Kari Anker Jorgensen
Synthesis of 4,5-Disubstituted 2-aminothiazoles from , -Unsaturated Ketones: Preparation of S-benzyl-4-methyl-2-aminothiazolium Hydrochloride salt 185
Antonio Bermejo Gomez, Nanna Ahlsten, Ana E. Platero-Prats and Belen Martin-Matute
Sodium Methoxide-Catalyzed Direct Amidation of Esters 201
Kazushi Agura, Takashi Ohshima, Yukiko Hayashi, And Kazushi Mashima
Synthesis of Tetrasubstituted 1H-Pyrazoles by Copper-mediated Coupling of Enaminones with Nitriles 211
Mamta Suri and Frank Glorius
Synthesis of 1,3-Dimethyl-3-(p-tolyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one by Cu(II)-Mediated Direct Oxidative Coupling 221
Chandan Dey and E. Peter Kundig
Preparation of (R)-4-Cyclohexyl-2,3-butadien-1-ol 233
Juntao Ye and Shengming
Discussion Addendum for: Formation of y-Keto Esters from -Keto Esters: Methyl 5,5-dimethyl-4-oxohexanoate 248
Yashoda M. D. Bhogadhi and Charles K. Zercher
Ni-catalyzed Reductive Cleavage of Methyl 3-Methoxy-2-Naphthoate 260
Josep Cornella, Cayetana Zarate, and Ruben Martin
Indium-Catalyzed Heteroaryl-Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2-Methyl-3-(thien-2-yl)-1H-indole 273
Yuta Nagase and Teruhisa Tsuchimoto
Synthesis of 2,3-Disubstituted Benzofurans by the Palladium-Catalyzed Coupling of 2-Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization: 3-Iodo-2-phenylbenzofuran 283
Tuanli Yao, Dawei Yue, and Richard C. Larock
Enantioselective Preparation of (S)-5-Oxo-5,6-dihydro-2H-oyran-2-yl Benzoate 293
Tamas Benkovics, Adrian Ortiz, Zhiwei Guo, Animesh Goswami and Prashant Deshpande
Iron-Catalyzed Selective Conjugate Addition of Aryl Grignard Reagents to 2,4-Alkadienoates: tert-Butyl (Z)-5-Phenyl-3-hexenoate 307
Takeshi Hata, Hideyuki Goto, Tomofumi Yokomizo, and Hirokazu Urabe
3-Hydrixymethyl-3-phenylcyclopropene 322
Ramajeyam Selvaraj, Srinvasa R. Chintala, Michael T. Taylor and Joseph M. Fox
Enantioselective Synthesis of - and -Boc-protected 6-Hydroxy-pyranones: Carbohydrate Building Blocks 338
Sumit O. Bajaj, Jamison R. Farnsworth and George A. O'Doherty
- Volume
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v. 92 ISBN 9781119280682
Description
The current volume continues the tradition of the Organic Synthesis series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including phar-maceuticals, fine chemicals, agrochemicals, and biotech.
- Volume
-
v. 93 ISBN 9781119349020
Description
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Table of Contents
DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime 1
Taku Imaizumi, Kentaro Okano, and Hidetoshi Tokuyama
Preparation of 2-(2-(Dicyclohexylphosphino)phenyl)-1-methyl-1H-indole (CM-phos) 14
Shun Man Wong, On Ying Yuen, Pui Ying Choy, Chau Ming So, and Fuk Yee Kwong
Synthesis of 5-(Hydroxymethyl)furfural (HMF) 29
Svilen P. Simeonov, Jaime A. S. Coelho, and Carlos A. M. Afonso
Erratum for: Titanium-Mediated Addition of Silyl Dienol Ethers to Electrophilic Glycine: 4 Ketopipecolic Acid Hydrochloride 37
Clarisse Muhlemann, Peter Hartmann, and Jean-Pierre Obrecht
Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate 50
Alexander C. Wotal, Donald C. Batesky, and Daniel J. Weix
Trichloroboron-promoted Deprotection of Phenolic Benzyl Ether UsingPentamethylbenzene as a Non Lewis-Basic Cation Scavenger 63
Shun Okaya, Keiichiro Okuyama, Kentaro Okano, and Hidetoshi Tokuyama
Enantioselective Synthesis of , -Disubstituted Lactones via a Chiral Bronsted Acid-Catalyzed Intramolecular Cyclization 75
Jennifer E. Wilent, Ghassan Qabaja, and Kimberly S. Petersen
Enantioselective Synthesis of -Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate 88
Victoria T. Lim, Sergey V. Tsukanov, Amanda B. Stephens, and Jeffrey N. Johnston
Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde 100
Matthias Schulze, Alexander Scherer, Colin Diner, and Rik R. Tykwinski
Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I) 115
M. Elena de Orbe and Antonio M. Echavarren
Photochemical Benzannulation of N-Phosphoryl Ynamides and -Diazo Ketones in Continuous Flow 127
John M. Read, Yu-Pu Wang, and Rick L. Danheiser
Trifluoromethylation of Aryl Iodides Catalyzed by the Copper(I)-Phen Complex 147
Naoto Shimizu, Hideaki Kondo, Masahiro Oishi, Kenichi Fujikawa, Kazuki Komoda, and Hideki Amii
Copper-catalyzed Cyanation of Alkenyl Iodides 163
Antoine Nitelet, Sara Zahim, Cedric Theunissen, Alexandre Pradal, and Gwilherm Evano
Visible Light Photocatalysis of Radical Cation Diels-Alder Cycloadditions: Preparation of Tris(2,2'-bipyrazyl) Ruthenium(II) Bis(tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) 178
Shane D. Lies, Shishi Lin, and Tehshik P. Yoon
Preparation of Methyl 1,2,3,4-tetra-O-acetyl- -D-glucopyranuronate 200
Aisling Ni Cheallaigh, Garrett T. Potter, John M. Gardiner, and Gavin J. Miller
Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one 210
Robert A. Craig, II, Russell C. Smith, Beau P. Pritchett, Benzi I. Estipona, and Brian M. Stoltz
Oxyboration: Synthesis of Borylated Benzofurans 228
Darius J. Faizi, Nicole A. Nava, Mohammad Al-Amin, and Suzanne A. Blum
Synthesis of 1-Iodopropyne 245
Samuel G. Bartko, James Deng, and Rick L. Danheiser
Potassium tert-Butoxide-Catalyzed Dehydrogenative Cross-Coupling of Heteroarenes with Hydrosilanes 263
Anton A. Toutov, Wen-Bo Liu, Brian M. Stoltz, and Robert H. Grubbs
Synthesis of -Carboline 272
Linli He, Shawn P. Allwein, Benjamin J. Dugan, Kyle W. Knouse, Gregory R. Ott, and Craig A. Zificsak
Synthesis of Methyl 1-Formylcyclopropanecarboxylate utilizing Ti-Claisen Condensation 286
Yuichiro Ashida, Satomi Kajimoto, Hidefumi Nakatsuji, and Yoo Tanabe
Nickel-Catalyzed Suzuki-Miyaura Coupling in t-Amyl Alcohol for the Preparation of 5-(Furan-3-yl)pyrimidine 306
Liana Hie and Neil K. Garg
Preparation of (S)-Nonafluorobutanesulfinamide 319
Apiwat Wangweerawong, Scott Kolmar, and Jonathan A. Ellman
Preparation of 1-Methylimidazole-N-oxide (NMI-O) 331
James I. Murray and Alan C. Spivey
Palladium-Catalyzed Direct Amination of Allylic Alcohols at Room Temperature 341
Bao Gao, Lixin Li, Guoying Zhang, and Hanmin Huang
Preparation of 1,1-Difluoroallenes by Difluorovinylidenation of Carbonyl Compounds 352
Kohei Fuchibe, Masashi Abe, Ken Oh, and Junji Ichikawa
Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters 367
Stephanie Ganss, Julia Pedroni, Alexandre Lumbroso, Gunther Leonhardt-Lutterbeck, Antje Meissner, Siping Wei, Hans-Joachim Drexler, Detlef Heller, and Bernhard Breit
Copper-Catalyzed Semi-Reduction of Alkynes 385
Nick Cox, Hester Dang, Aaron M. Whittaker, and Gojko Lalic
Synthesis of Cyclobutanes by Lewis Acid-Promoted Ketene-Alkene [2+2] Cycloadditions 401
Christopher M. Rasik, Eleni M. Salyers, and M. Kevin Brown
Synthesis of 2,2-Dichloroimidazolidine-4,5-diones and their Application in Chlorodehydroxylation 413
David Schilter and Christopher W. Bielawski
- Volume
-
v. 94 ISBN 9781119511946
Description
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Table of Contents
Preparation of Aryl Alkyl Ketenes 1
Nicholas D. Staudaher, Joseph Lovelace, Michael P. Johnson, and Janis Louie
Preparation of Diisopropylammonium Bis(catecholato)cyclohexylsilicate 16
Kingson Lin, Christopher B. Kelly, Matthieu Jouffroy, and Gary A.Molander
Continuous Flow Hydration of Pyrazine-2-carbonitrile in a Manganese Dioxide Column Reactor 34
Claudio Battilocchio, Shing-Hing Lau, Joel M. Hawkins, and Steven V. Ley
Site-Selective C-H Fluorination of Pyridines and Diazines with AgF2 46
Patrick S. Fier and John F. Hartwig
Site-Selective C-H Fluorination of Pyridines and Diazines with AgF2 46
Patrick S. Fier and John F. Hartwig
Ugi Multicomponent Reaction 54
Andre Boltjes, Haixia Liu, Haiping Liu, and Alexander Doemling
Palladium-catalyzed External-CO-Free Reductive Carbonylation of Bromoarenes 66
Hideyuki Konishi, Masataka Fukuda, Tsuyoshi Ueda, and Kei Manabe
Practical Syntheses of [2,2'-bipyridine]bis[3,5-difluoro-2- [5-(trifluoromethyl)-2 pyridinyl]phenyl]iridium(III) hexafluorophosphate, [Ir{dF(CF3)ppy}2(bpy)]PF6 and [4,4'-bis (tert-butyl) 2,2'-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate, [Ir{dF(CF3)ppy}2 (dbbpy)]PF6 77
Martins S. Oderinde and Jeffrey W. Johannes
(Z)-Enol p-Tosylate Derived from Methyl Acetoacetate: A Useful Cross-coupling Partner for the Synthesis of Methyl (Z)-3-Phenyl (or Aryl)-2-butenoate 93
Yuichiro Ashida, Hidefumi Nakatsuji, and Yoo Tanabe
Synthesis of Allenyl Mesylate by a Johnson-Claisen Rearrangement. Preparation of 3-(((tert-butyldiphenyl- silyl)oxy)methyl)penta-3,4-dien-1-yl methanesulfonate 109
Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond
Rhodium(I)-catalyzed Allenic Pauson-Khand Reaction 123
Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond
Dirhodium (II) tetrakis[N-4-bromo-1,8-naphthoyl-(S)-tert-leucinate] 136
Helene Lebel, Henri Piras, and Johan Bartholomeus
Buta-2,3-dien-1-ol 153
Hongwen Luo, Dengke Ma, and Shengming Ma
Fragment Coupling and Formation of Quaternary Carbons by Visible-Light Photoredox Catalyzed Reaction of tert-Alkyl Hemioxalate Salts and Michael Acceptors 167
Christopher R. Jamison, Yuriy Slutskyy, and Larry E. Overman
N-Methoxy-N-methylcyanoformamide 184
Jeremy Nugent and Brett D. Schwartz
4-Cyano-2-methoxybenzenesulfonyl Chloride 198
Elliott D. Bayle, Niall Igoe, and Paul V. Fish
Preparation of N-Trifluoromethylthiosaccharin: A Shelf-Stable Electrophilic Reagent for Trifluoromethylthiolation 217
Jiansheng Zhu, Chunhui Xu, Chunfa Xu, and Qilong Shen
Homologation of Boronic Esters with Lithiated Epoxides 234
Roly J. Armstrong and Varinder K. Aggarwal
Asymmetric Michael Reaction of Aldehydes and Nitroalkenes 252
Yujiro Hayashi and Shin Ogasawara
Preparation of anti-1,3-Amino Alcohol Derivatives Through an Asymmetric Aldol-Tishchenko Reaction of Sulfinimines 259
Pamela Mackey, Rafael Cano, Vera M. Foley, and Gerard P. McGlacken
Rhenium-Catalyzed ortho-Alkylation of Phenols 280
Yoichiro Kuninobu, Masaki, Yamamoto, Mitsumi Nishi, Tomoyuki Yamamoto, Takashi Matsuki, Masahito Murai, and Kazuhiko Takai
Enantioselective Preparation of 5-Oxo-5,6-dihydro-2H-pyran-2-yl phenylacetate via organocatalytic Dynamic Kinetic Asymmetric Transformation (DyKAT) 292
Tamas Benkovics, Adrian Ortiz, Gregory L. Beutner, and Chris Sfouggatakis
Preparation of Sodium Heptadecyl Sulfate (Tergitol-7i) 303
Brent A. Banasik and Mansour Samadpour
Catalytic Enantioselective Addition of Diethyl Phosphite to N-Thiophosphinoyl Ketimines: Preparation of (R)-Diethyl (1-Amino-1-phenylethyl)phosphonate 313
Shaoquan Lin, Yasunari Otsuka, Liang Yin, Naoya Kumagai, and Masakatsu Shibasaki
Water-promoted, Open-flask Synthesis of Amine-boranes: 2-Methylpyridine-borane (2-Picoline-borane) 332
Ameya S. Kulkarni and P. Veeraraghavan Ramachandran
Preparation of N-Sulfinyl Aldimines using Pyrrolidine as Catalyst via Iminium Ion Activation 346
Sara Morales, Alfonso Garcia Rubia, Eduardo Rodrigo, Jose Luis Acena, Jose Luis Garcia Ruano, and M. Belen Cid
Synthesis of N-Boc-N-Hydroxymethyl-L-phenylalaninal 358
Jae Won Yoo, Youngran Seo, Dongwon Yoo, and Young Gyu Kim
Synthesis of Methyl trans-Oxazolidine-5-carboxylate, a Chiral Synthon for threo- -Amino- -hydroxy Acid 372
Youngran Seo, Jae Won Yoo, Yoonjae Lee, Boram Lee, Bonghyun Kim, and Young Gyu Kim
Preparation of Benzyl((R)-2-(4-(benzyloxy)phenyl)-2-((tert- butoxycarbonyl)amino)acetyl)-D-phenylalaninate using Umpolung Amide Synthesis 388
Matthew T. Knowe, Sergey V. Tsukanov, and Jeffrey N. Johnston
- Volume
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v. 95 ISBN 9781119595397
Description
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Table of Contents
Copper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and , -Unsaturated Aldehydes 1
Wei Wen Tan, Bin Wu, Ye Wei, and Naohiko Yoshikai
An Au/Zn-catalyzed Synthesis of N-Protected Indole via Annulation of N-Arylhydroxamic Acid and Alkyne 15
Xinpeng Cheng, Yanzhao Wang, and Liming Zha
Preparation of Fac-Tris(2-Phenylpyridinato) Iridium(III) 29
Kip A. Teegardin and Jimmie D. Weaver
Preparation of Cyclopent-2-enone Derivatives via the Aza-Piancatelli Rearrangement 46
Meghan F. Nichol, Luis Limon, and Javier Read de Alaniz
Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles 60
Kyle M. Lambert, Sherif A. Eldirany, James M. Bobbitt, and William F. Bailey
Copper-Catalyzed Enantioselective Hydroamination of Alkenes 80
Richard Y. Liu and Stephen L. Buchwald
Preparation of 6H-Benzo[c]chromen-6-one 97
Yang Wang, Yi Shi, and Vladimir Gevorgya
Synthesis of N-Acyl Pyridinium-N-Aminides and Their Conversion to 4-Aminooxazoles via a Gold-Catalyzed Formal (3+2)-Dipolar Cycloaddition 112
Matthew P. Ball-Jones and Paul W. Davies
Preparation of Solid Organozinc Pivalates and Their Reaction in Pd-Catalyzed Cross-Couplings 127
Mario Ellwart, Yi-Hung Chen, Carl Phillip Tullmann, Vladimir Malakhov, and Paul Knochel
Enantioselective Synthesis of (S)-Ethyl 2-((tert-butoxycarbonyl)((tertbutyldimethylsilyl) oxy)amino)-4 oxobutanoate 142
Thibault J. Harmand, Claudia E. Murar, Hikaru Takano, and Jeffrey W. Bode
Preparation of (S)-N-Boc-5-oxaproline 157
Claudia E. Murar, Thibault J. Harmand, Hikaru Takano, and Jeffrey W. Bode
Syntheses of Substituted 2-Cyano-benzothiazoles 177
Hendryk Wurfel and Doerthe Jakobi
Preparation of N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ylidene) nitramide 192
Emerson Teixeira da Silva, Adriana Marques Moraes, Adriele da Silva Araujo, and Marcus Vinicius Nora de Souza
Preparation of Alkyl Boronic Esters Using Radical-Polar Crossover Reactions of Vinylboron Ate Complexes 205
Marvin Kischkewitz and Armido Studer
Preparation of (pin)B-B(dan) 218
Hiroto Yoshida, Yuya Murashige, and Itaru Osaka
Discussion Addendum for: Preparation of a Carbazole-Based Macrocycle Via Precipitation-Driven Alkyne Metathesis 231
Christopher C. Pattillo, Morgan M. Cencer, and Jeffrey S. Moore
Hydrodecyanation by a Sodium Hydride-Iodide Composite 240
Guo Hao Chan, Derek Yiren Ong, and Shunsuke Chiba
Indole-Catalyzed Bromolactonization: Preparation of Bromolactone in Lipophilic Media 256
Zhihai Ke, Tao Chen, and Ying-Yeung Yeung
Discussion Addendum for: Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation [(E)-Methyl 3-phenyloct-2-enoate] 267
Yoshihiko Yamamoto
Modified McFadyen-Stevens Reaction for a Versatile Synthesis of Aromatic Aldehydes 276
Yuri Iwai and Jun Shimokawa
Discussion Addendum for: Facile Syntheses of Aminocyclopropanes: N,N-Dibenzyl-N-(2-ethenylcyclopropyl)amine [(Benzenemethanamine, N-(2-ethenylcyclopropyl)-N-(phenylmethyl)) 289
Armin de Meijere and Sergei I. Kozhushkov
(R)-2,2,2-Trichloro-1-phenylethyl (methylsulfonyl)oxycarbamate 310
Helene Lebel, Henri Piras, and Johan Bartholomeus
Large Scale Synthesis of Enantiomerically Pure (S)-3-(4-Bromophenyl)- butanoic Acid 328
J. Craig Ruble, H. George Vandeveer, and Antonio Navarro
Preparation of Tributyl(iodomethyl)stannane 345
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Stannylamine Protocol (SnAP) Reagents for the Synthesis of C-Substituted Morpholines from Aldehydes 357
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Trimethylsilyldiazo[13C]methane: A Versatile 13C-Labelling Reagent 374
Chris Nottingham and Guy C. Lloyd-Jones
Stereoretentive Iron-catalyzed Cross-coupling of an Enol Tosylate with MeMgBr 403
Takeshi Tsutsumi, Yuichiro Ashida, Hiroshi Nishikado, and Yoo Tanabe
Synthesis of Methyl 2-Bromo-3-oxocyclopent-1-ene-1-carboxylate 425
Rama Rao Tata and Michael Harmata
Discussion Addendum for: Preparation of (S)-tert-ButylPHOX and (S)-2-Allyl-2-Methylcyclohexanone 439
Alexander W. Sun and Brian M. Stoltz
Synthesis of Acyl Derivatives of Cotarnine 455
Laxmidhar Rout, Bibhuti Bhusan Parida, Ganngum Phaomei, Bertounesque Emmanuel, and Akhila Kumar Sahoo
Carbonyl-Olefin Metathesis for the Synthesis of Cyclic Olefins 472
Marc R. Becker, Katie A. Rykaczewski, Jacob R. Ludwig, and Corinna S. Schindler
Hexafluoro-2-propanol-promoted Intramolecular Friedel-Crafts Acylation 486
Rakesh H. Vekariya, Matthew C. Horton, and Jeffrey Aube
Discussion Addendum for: Preparation of the COP Catalysts: [(S)-COP-OAc]2, [(S)-COP-Cl]2, and (S)-COP-hfacac 500
Jeffrey S. Cannon and Larry E. Overman
- Volume
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v. 96 ISBN 9781119707769
Description
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Table of Contents
Discussion Addendum for: 4-Nonylbenzoic Acid 1
Alois Furstner
Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix 16
Junting Chen and Tobias Ritter
Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 36
Yuki Kawashima, Takayuki Furukawa, Naoto Chatani and Mamoru Tobisu
Discussion Addendum for: Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to , -Unsaturated Esters: Asymmetric Synthesis of (S)- -Leucine 53
Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, and James E. Thomson
Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates 66
Mi-Na Zhao and Zheng-Hui Guan
Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2- (2-acetylphenyl)acetate 80
Austin C. Wright and Brian M. Stoltz
Discussion Addendum for: Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate 98
Mizzanoor Rahaman and M. Mahmun Hossain
Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate 110
Aslam C. Shaikh and Ohyun Kwon
Discussion Addendum for: Protection of Alcohols using 2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-methyl Propanoate 124
Harvey F. Fulo, Philip A. Albiniak, and Gregory B. Dudley
Synthesis of 4-Methylbenzoate(2',4',6'-trimethoxy-phenyl)iodonium Tosylate 137
Thomas L. Seidl, Aaron Moment, Charles Orella, Thomas Vickery, and David R. Stuart
Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes 150
Chris Nottingham, Verity Barber, and Guy C. Lloyd-Jones
Discussion Addendum for: Preparation of Enantioenriched Homoallylic Primary Amines 179
Miguel Yus
Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide 195
Cedric Theunissen, Pierre Thilmany, Mounsef Lahboubi, Nicolas Blanchard, and Gwilherm Evano
Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate 214
Aslam C. Shaikh and Ohuyn Kwon
Discussion Addendum for: Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines 232
Miguel Yus
Synthesis of Chiral Diamine Ligands for Nickel-catalyzed Asymmetric Cross-couplings of Alkylchloroboronate Esters with Alkylzincs: 1R,2R)-N,N'-Dimethyl-1,2-bis(2-methylphenyl)-1,2-diaminoethane 245
Yusuke Masuda and Gregory C. Fu
Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d] thiophenium triflate 258
Bernd Waldecker, Kevin Kafuta, and Manuel Alcarazo
Three-Step Synthesis of 2-(Diiodomethyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane from Dichloromethane 277
Morgane Sayes, Guillaume Benoit, and Andre B. Charette
Discussion Addendum for: Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ -caprolactamate] of tert-Butyldimethylsilylprotected trans-Dehydroandrosterone 300
Yong-Liang Su, Luca De Angelis and Michael P. Doyle
Preparation of (R)-3-(3,5-Bistrifluoromethylphenyl)-1,1'-bi-2-naphthol 312
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Catalytic Enantioselective Addition of an In-Situ Prepared Aryltitanium Reagent to p-Chloroacetophenone: (R)-(+)-1-(4-Chlorophenyl)-1-m-tolylethanol 333
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Stereoselective Synthesis of (R)-((R)-1-Phenyl-2,2,2-trichloroethyl)-2-(2-bromophenyl)aziridine-1-carboxylate 351
Helene Lebel and Henri Piras
Discussion Addendum for: Preparation of (R,R)-1,2:4,5-Diepoxypentane 361
Nicholas Sizemore and Scott D. Rychnovsky
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine 382
Scott E. Denmark and Pavel Ryabchuk
Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification 400
Scott E. Denmark, Pavel Ryabchuk, Hyung Min Chi, and Anastassia Matviitsuk
anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide 418
Trevor V. Nykaza, Julian C. Cooper, and Alexander T. Radosevich
Facile Reduction of Amides Using Nickel Catalysis: Reduction of 12-Aminododecanolactam 436
Bryan J. Simmons, Melissa Ramirez, and Neil K. Garg
Preparation of 2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile 455
Saskia M. Engle, Takisha R. Kirkner, and Christopher B. Kelly
Discussion Addendum for: Fluorobis(phenylsulfonyl)methane (FBSM) 474
Xanath Ispizua-Rodriguez, Vinayak Krishnamurti, Mathew Coe, and G. K. Surya Prakash
Synthesis of 5-Hydroxy-4-methoxy-2-methylpyrylium Trifluoromethanesulfonate from Kojic Acid 494
Nana B. Agyemang and Ryan P. Murelli
Iridium-Catalyzed Reductive Coupling of Grignard Reagents and Tertiary Amides 511
Pablo Gabriel, Lan-Gui Xie, and Darren J. Dixon
Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride 528
Kyle M. Lambert, Austin W. Medley, Amy C. Jackson, Lauren E. Markham, and John L. Wood
Synthesis of 8-Hydroxygeraniol 586
Francesca M. Ippoliti, Joyann S. Barber, and Neil K. Garg
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