Acid catalysis in modern organic synthesis
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書誌事項
Acid catalysis in modern organic synthesis
Wiley-VCH, c2008
- v. 1
- v. 2
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注記
Includes bibliographical references and index
内容説明・目次
内容説明
This two-volume set covers all new developments and, in addition, includes the hot concept of combined Bronsted and Lewis acid catalysis, developed by Hisashi Yamamoto himself. The excellent editorial team has put together an equally top team of expert authors, resulting in a true treasure trove of essential information -- making this a must for every chemist working in organic chemistry and catalysis, in academia as well as in industry.
目次
Preface XIX
List of Contributors XXI
Volume 1
1 Recent Advance of 'Combined Acid' Strategy for Asymmetric Catalysis 1
Hisashi Yamamoto and Kentaro Futatsugi
1.1 Combined Acid Catalysis 1
1.2 Super Bronsted Acid Catalyst 29
1.3 Combined Super Bronsted Acid and Lewis Acid System 31
1.4 Conclusion 31
2 Bronsted Acids 35
2.1 Super Bronsted Acid 35
Hisashi Yamamoto, Daisuke Nakashima
2.2 Chiral Bronsted Acids 62
Takahiko Akiyama
3 Li(I), Na(I), and K(I) Lewis Acids 109
Tatsushi Imahori
3.1 Introduction 109
3.2 Alkali Metal Salts as Lewis Acid Reaction Promoter 109
3.3 Lewis Acid Property of Alkali Metals in Organoalkali Metal Reagents 125
3.4 Closing Remarks 130
4 Mg(II), Ca(II), and Zn(II) Lewis Acids 135
Manabu Hatano and Kazuaki Ishihara
4.1 Introduction 135
4.2 Mg(II)-Catalyzed Reactions 136
4.3 Ca(II)-Catalyzed Reactions 149
4.4 Zn(II)-Catalyzed Reactions 151
4.5 Reaction with Mg(II) and Zn(II) Ate Complexes 175
5 Boron (III) Lewis Acids 187
Vivek Rauniyar and Dennis G. Hall
5.1 Introduction 187
5.2 Cycloaddition Reactions 188
5.3 Other Ring-Forming Reactions 196
5.4 Rearrangements and Isomerization Reactions 203
5.5 Nucleophillic Additions to Carbonyl and Imine Compounds 209
5.6 Miscellaneous Reactions 222
5.7 New Types of Boron-Based Lewis Acids 234
5.8 Conclusion 236
6 Al(III) Lewis Acids 241
Takeo Taguchi and Hikaru Yanai
6.1 Introduction 241
6.2 Alkylation 241
6.3 Friedel-Crafts Reactions 245
6.4 Aldol Reactions 250
6.5 Ene Reactions 256
6.6 Carbonyl Additions and Related Reactions 260
6.7 Strained Heterocycles Opening Reactions 279
6.8 Michael Addition Reactions 286
6.9 Cycloaddition Reactions 295
6.10 Claisen Rearrangement 327
6.11 Radical Reactions 331
7 Ga(III) Lewis Acids 347
Ryo Amemiya and Masahiko Yamaguchi
7.1 Introduction 347
7.2 Lewis Acid Activation by Interactions with n Electrons 348
7.3 Lewis Acid Activation by the Interactions with Electrons 359
7.4 Lewis Acid Activation by Interactions with Electrons 367
7.5 Homolysis of Organogallium(III) Compounds 368
7.6 Conclusions 371
8 In(III) Lewis Acids 377
Guan-Leong Chua and Teck-Peng Loh
8.1 Introduction 377
8.2 Aldol and Related Reactions 377
8.3 1,2-Additions to Aldehydes, Ketones and their Synthetic Equivalents 381
8.4 1,4-Addition 391
8.5 Additions to C=N 396
8.6 Ring Opening of Aziridines and Oxiranes 400
8.7 Other Addition Reactions 403
8.8 Electrophilic Aromatic Substitutions 408
8.9 Nucleophilic Substitutions 413
8.10 Cycloaddition Reactions 421
8.11 Prins-type Cyclizations 427
8.12 Other Cyclization Reactions 432
8.13 Oxidations and Reductions 440
8.14 Protection/Deprotection 443
8.15 Miscellaneous Reactions 446
8.16 Asymmetric Catalysis by Chiral Indium Complexes 454
8.17 Conclusion 458
9 Si(IV) Lewis Acids 469
Akira Hosomi and Katsukiyo Miura
9.1 Introduction 469
9.2 Synthetic Use of Silicon Lewis Acids 470
9.3 R3SiX-Promoted Reactions of Acetals and Their Precursors 473
9.4 R3SiX-Promoted Reactions of Carbonyl Compounds 485
9.5 R3SiX-Promoted Reactions of Imines, Aminoacetals, and Related Compounds 496
9.6 R3SiX-Promoted Reactions of Ethers, Esters, Alcohols, and Halides 499
9.7 Other R3SiX-Promoted Reactions 502
9.8 Strained Organosilicon Lewis Acids 503
9.9 Silicon Lewis Acids Activated by Lewis Bases 506
9.10 Concluding Remarks 509
10 Sn(II) and Sn(IV) Lewis Acids 517
Isamu Shiina and Hiroki Fukui
10.1 Introduction 517
10.2 Cycloadditions 517
10.3 Ring-Opening Reactions and Rearrangements 523
10.4 Olefin Activation Reactions 528
10.5 Carbonyl Activation Reactions Including Mukaiyama-Type Reactions 532
10.6 Other Reactions 545
10.7 Conclusions 547
Volume 2
11 Bismuth (III) Lewis Acids 551
Hafida Gaspard-Iloughmane and Christophe Le Roux
11.1 Introduction 551
11.2 Nucleophilic Additions 552
11.3 Cyclization Reactions 560
11.4 Electrophilic Additions 565
11.5 Rearrangements 567
11.6 Ring Opening Reactions 569
11.7 Protection and Deprotection 573
11.8 Oxidation and Reduction Reaction 576
11.9 Miscellaneous Reactions 578
11.10 Green Conditions Involving Bismuth(III) Salts 581
11.11 Conclusion 582
12 Scandium and Yttrium 589
Chikako Ogawa, Yanlong Gu, Marine Boudou and Shu Kobayashi
12.1 Achiral Reactions in Organic Solvent or Solvent-Free Conditions 589
12.2 Asymmetric Reactions in Organic Solvents 606
12.3 Scandium-Catalyzed Reactions in Aqueous Media 620
12.4 Yttrium 625
13 Lanthanide Lewis Acid 635
Masakatsu Shibasaki, Shigeki Matsunaga and Naoya Kumagai
13.1 Introduction 635
13.2 Achiral Lanthanide Lewis Acid Catalysis 636
13.3 Chiral Lanthanide Lewis Acid Catalysis 656
13.4 Lanthanide Bimetallic and Polymetallic Asymmetric Catalysts 670
13.5 Lanthanide-Alkali Metal Heterobimetallic Asymmetric Catalysts 694
13.6 Conclusion 710
14 Titanium Lewis Acid 721
Yu Yuan, Kuiling Ding and Gang Chen
14.1 Introduction 721
14.2 Alkylation, Alkynylation, Vinylation, and Arylation 722
14.3 Allylation 732
14.4 Aldol Reaction 739
14.5 Carbonyl-Ene Reaction 747
14.6 Cycloaddition Reactions 753
14.7 Cyanation 768
14.8 Ring-Opening of Epoxides 777
14.9 Friedel-Crafts Reaction 780
14.10 Baylis-Hillman Reaction 781
14.11 Epoxidation 782
14.12 Sulfoxidation 786
14.13 Halogenation 790
14.14 Reduction 792
14.15 Hydroamination 794
14.16 Miscellaneous 801
14.17 Summary and Outlook 805
15 Zr(IV) and Hf(IV) Lewis Acids 825
Ken-ichiro Kanno and Tamotsu Takahashi
15.1 Introduction 825
15.2 Aldol Reactions 825
15.3 Friedel-Crafts Reactions 834
15.4 Allylations with Allylstannanes 837
15.5 Ring Opening of Three-Membered Cyclic Compounds 839
15.6 Pericyclic Cycloadditions 842
15.7 Carbometalations 846
15.8 Functional Group Transformations 849
16 Transition-Metal Lewis Acids: From Vanadium to Platinum 859
Seiji Iwasa and Hisao Nishiyama
16.1 Introduction 859
16.2 Carbon-Carbon Bond-Forming Reactions 860
16.3 Carbon-Heteroatom Bond-Forming or Cleaving Reactions 891
16.4 Conclusion 897
17 Cu(I) and Cu(II) Lewis Acids 903
Levi M. Stanley and Mukund P. Sibi
17.1 Introduction 903
17.2 Friedel-Crafts Reactions 905
17.3 Claisen Rearrangements 908
17.4 Free-Radical Reactions 909
17.5 Nucleophilic Addition to C=O and C=N Double Bonds 911
17.6 Conjugate Additions 938
17.7 Cycloadditions 943
17.8 Ene Reactions 970
17.9 Nazarov Cyclization 972
17.10 Alkylation, Amination, and Halogenation 973
17.11 Transfer Hydrogenation 976
17.12 Asymmetric Benzoylation 978
17.13 Theoretical Methods 978
17.14 Conclusions 980
18 Ag(I), Au(I), and Au(III) Lewis Acids 987
Akira Yanagisawa
18.1 Introduction 987
18.2 Achiral Silver(I)-Catalyzed Carbon-Carbon Bond Forming Reactions 987
18.3 Chiral Phosphine-Silver(I) Complex-Catalyzed Asymmetric Reactions 992
18.4 Gold(I) and Gold(III)-Catalyzed Carbon-Carbon Bond Forming Reactions 1004
18.5 Summary and Conclusions 1011
19 Polymer-Supported Metal Lewis Acids 1019
Shinichi Itsuno
19.1 Introduction 1019
19.2 Boron-Containing Polymeric Lewis Acid 1020
19.3 Polymer-Supported Aluminum Lewis Acids 1029
19.4 Polymer-Supported Sc Lewis Acids 1035
19.5 Polymer-Supported Ti Lewis Acids 1040
19.6 Polymer-Supported Fe Lewis Acids 1049
19.7 Polymer-Supported Cu Lewis Acids 1050
19.8 Polymer-Supported Zn Lewis Acids 1051
19.9 Polymer-Supported in Lewis Acids 1052
19.10 Polymer-Supported Sn Lewis Acids 1053
19.11 Polymer-Supported Yb Lewis Acids 1054
Index 1061
Reaction Index 1109
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