CiNii Books - Chiral ferrocenes in asymmetric catalysis : synthesis and applications

This book meets the long-felt need for a reference on ferrocenes with the focus on catalysis. It provides a thorough overview of the synthesis and characterization of different types of chiral ferrocene ligands, their application to various catalytic asymmetric reactions, and versatile chiral materials as well as drug intermediates synthesized from them. Written by the "who's who" of ferrocene catalysis, this is a guide to the design of new ferrocene ligands and synthesis of chiral synthetic intermediates, and will thus be useful for organic, catalytic and synthetic chemists working in academia, industrial research or process development.

Table of Contents

INTRODUCTION Foreword Planar Chirality of Ferrocenyl Ligands Derivatization of the Ferrocene Scaffold Stability, Rigidity and Bulkiness of the Ferrocene Scaffold Outlook STEREOSELECTIVE SYNTHESIS OF PLANAR CHIRAL FERROCENES Introduction Diastereoselective Directed Ortho-Metalation of Ferrocenes with Chiral Auxiliaries Enantioselective Directed Ortho-Metalation of Ferrocenes with Chiral Bases Enzymatic and Nonenzymatic Kinetic Resolutions Summary and Perspectives Selected Experimental Procedures MONODENTATE CHIRAL FERROCENYL LIGANDS Introduction Nickel-Catalyzed Asymmetric Reductive Coupling Reactions Copper(I)-Catalyzed Asymmetric Allylic Alkylation Reactions Asymmetric Suzuku-Miyaura Reactions Addition of Organoaluminum to Aldehydes and Enones Asymmetric Nucleophilic Catalysis Conclusions and Perspectives BIDENTATE 1,2-FERROCENYL DIPHOSPHINE LIGANDS Introduction Type A, Both PR2 Groups Attached to the Cp Ring Type B, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to the Alpha-Position of the Side Chain Type C, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to the Beta-Position of the Side Chain Type D, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to Other Positions of the Side Chain Type E, Both PR2 Groups Attached to Side Chains 1,2-P,N-BIDENTATE FERROCENYL LIGANDS Introduction Asymmetric Hydrogenation and Asymmetric Transfer Hydrogenation Formation of C-C Bond Cycloaddition Reactions Miscellaneous Reactions Conclusion and Perspectives Experimental: Selected Procedures N,O-BIDENTATE FERROCENYL LIGANDS Introduction Addition of Organozinc Reagents to Aldehydes Addition to Aldehydes with Boron Reagents Other Transformations: Asymmetric Epoxidation Conclusion and Perspectives Experimental: Selected Procedures SYMMETRICAL 1,1'-BIDENTATE FERROCENYL LIGANDS Introduction Symmetrical 1,1'-Disubstituted Ferrocenyl Ligands Symmetrical 1,1',2,2'-Tetrasubstituted Ferrocenyl Ligands Analogs of Ferrocenes: Symmetrical 1,1'-Bidentate Ruthenocenyl Ligands Conclusion and Perspectives Experimental: Selected Procedures UNSYMMETRICAL 1,1'-BIDENTATE FERROCENYL LIGANDS Introduction Palladium-Catalyzed Asymmetric Allylic Substitution Reaction Gold or Silver-Catalyzed Asymmetric Aldol Reactions Asymmetric Hydrogenation Asymmetric Cross-Coupling Reaction Asymmetric Heck Reaction Miscellaneous Conclusion and Perspectives Experimental: Selected Procedures SULFUR- AND SELENIUM-CONTAINING FERROCENYL LIGANDS Introduction Asymmetric Allylic Substitution Other Asymmetric Palladium-Catalyzed Reactions Gold-Catalyzed Reactions Asymmetric Reductions Asymmetric 1,2- and 1,4-Nucleophilic Addition Asymmetric Cycloaddition Reactions Asymmetric Nucleophilic Catalysis Conclusion and Perspectives Experimental: Selected Procedures BIFERROCENE LIGANDS Introduction Trans-Chelating Chiral Bisphosphines: TRAP 2,2-Bis(diarylphosphino)-1,1-Biferrocenes: BIFEP Miscellaneous Biferrocene-Based Chiral Ligands Conclusion APPLICATIONS OF AZA- AND PHOSPHAFERROCENES AND RELATED COMPOUNDS IN ASYMMETRIC CATALYSIS Introduction Background on Aza- and Phosphaferrocenes Azaferrocenes in Catalysis Phosphaferrocenes in Catalysis Conclusions METALLOCYCLIC FERROCENYL LIGANDS Introduction Asymmetric Synthesis of Planar Chiral Metallocylic Complexes Stoichiometric Synthetic Applications of Scalemic Planar Chiral Metallocyclic Complexes Asymmetric Catalysis with Scalemic Planar Chiral Palladocyclic Complexes Conclusion SHOW CASE OF THE MOST EFFECTIVE CHIRAL FERROCENE LIGANDS IN VARIOUS CATALYTIC REACTIONS Asymmetric Allylic Substitution Reactions Asymmetric Aldol Reactions Asymmetric Cycloaddition Reactions Asymmetric Hydrogenation Pd-Catalyzed Asymmetric Heck Reaction Addition of Organozinc Reagents Asymmetric Rearrangement of Allylic Imidates Cu-Catalyzed Cyclopropanation Coupling Reaction of Vinyl Bromide and 1-Phenylethylzinc Chloride Enantioselective Intramolecular Aminopalladation Nickel-Catalyzed Asymmetric Three-Component Coupling of Alkynes, Imines, and Organoboron Reagents Reactions with Ketenes Ring Opening Reaction

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Chiral ferrocenes in asymmetric catalysis : synthesis and applications

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