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Full Description
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.
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
