InhaltsangabeINTRODUCTION 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 NickelCatalyzed 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 1,2P,NBIDENTATE 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,OBIDENTATE 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 PalladiumCatalyzed 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 SELENIUMCONTAINING FERROCENYL LIGANDS Introduction Asymmetric Allylic Substitution Other Asymmetric Palladium-Catalyzed Reactions GoldCatalyzed 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 TransChelating Chiral Bisphosphines: TRAP 2,2Bis(diarylphosphino)1,1Biferrocenes: 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 PdCatalyzed Asymmetric Heck Reaction Addition of Organozinc Reagents Asymmetric Rearrangement of Allylic Imidates CuCatalyzed Cyclopropanation Coupling Reaction of Vinyl Bromide and 1-Phenylethylzinc Chloride Enan

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Li-Xin Dai is Professor at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. He graduated from Zhejiang University in 1947 and joined the SIOC in 1953. He is the Honorary President of Shanghai Society of Chemistry and Chemical Industry, and the Chairman of the Academic Committee of the State Key Laboratory of Elemento-Organic Chemistry in Nankai University. His research interests include the design of chiral ligands and their applications in asymmetric catalysis. He was elected as the Member of the Chinese Academy of Sciences in 1993. He has authored over 150 scientific publications and has received numerous scientific awards, including Ho Leung Ho Lee Prize and the National Natural Science Award of China. XueLong Hou received his PhD in 1986 from the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences under the mentorship of Professors Wei Yuan Huang of SIOC and Henry N.C. Wong of the Chinese University of Hong Kong. He was awarded an Alexander von Humboldt research fellowship and completed two years of postdoctoral research with Professor Emanuel Vogel at Cologne University, Germany. He is currently Professor at the SIOC and his research interests include OMCOS, the design of chiral ligands and their applications in asymmetric catalysis and the transformation of organic molecules under nonmetal conditions.

Introduction How to Introduce a Planar Chirality in a Ferrocene Skeleton? Monodentate Chiral Ferrocenyl Ligands Bidentate 1,2-Ferrocenyl Diphosphine Ligands 1,2-P, N-Bidentate-Ferrocenyl Ligands N,O-Bidentate Ferrocenyl Ligands Symmetrical 1,1''-Bidentate Ferrocenyl Ligands Unsymmetrical 1,1''-Bidentate Ferrocenyl Ligands Sulfur, Selenium Containing Ferrocenyl Ligands Biferrocenyl Ligands Applications of Aza- and Phosphaferrocenes and Related Compounds in Asymmetric Catalysis Metallocyclic Ferrocenyl Ligands