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.

List of contents

INTRODUCTIONForewordPlanar Chirality of Ferrocenyl LigandsDerivatization of the Ferrocene ScaffoldStability, Rigidity and Bulkiness of the Ferrocene ScaffoldOutlookSTEREOSELECTIVE SYNTHESIS OF PLANAR CHIRAL FERROCENESIntroductionDiastereoselective Directed Ortho-Metalation of Ferrocenes with Chiral AuxiliariesEnantioselective Directed Ortho-Metalation of Ferrocenes with Chiral BasesEnzymatic and Nonenzymatic Kinetic ResolutionsSummary and PerspectivesSelected Experimental ProceduresMONODENTATE CHIRAL FERROCENYL LIGANDSIntroductionNickel-Catalyzed Asymmetric Reductive Coupling ReactionsCopper(I)-Catalyzed Asymmetric Allylic Alkylation ReactionsAsymmetric Suzuku-Miyaura ReactionsAddition of Organoaluminum to Aldehydes and EnonesAsymmetric Nucleophilic CatalysisConclusions and PerspectivesBIDENTATE 1,2-FERROCENYL DIPHOSPHINE LIGANDSIntroductionType A, Both PR2 Groups Attached to the Cp RingType B, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to the Alpha-Position of the Side ChainType C, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to the Beta-Position of the Side ChainType D, One PR2 Group Attached to the Cp Ring, One PR2 Group Attached to Other Positions of the Side ChainType E, Both PR2 Groups Attached to Side Chains1,2-P,N-BIDENTATE FERROCENYL LIGANDSIntroductionAsymmetric Hydrogenation and Asymmetric Transfer HydrogenationFormation of C-C BondCycloaddition ReactionsMiscellaneous ReactionsConclusion and PerspectivesExperimental: Selected ProceduresN,O-BIDENTATE FERROCENYL LIGANDSIntroductionAddition of Organozinc Reagents to AldehydesAddition to Aldehydes with Boron ReagentsOther Transformations: Asymmetric EpoxidationConclusion and PerspectivesExperimental: Selected ProceduresSYMMETRICAL 1,1'-BIDENTATE FERROCENYL LIGANDSIntroductionSymmetrical 1,1'-Disubstituted Ferrocenyl LigandsSymmetrical 1,1',2,2'-Tetrasubstituted Ferrocenyl LigandsAnalogs of Ferrocenes: Symmetrical 1,1'-Bidentate Ruthenocenyl LigandsConclusion and PerspectivesExperimental: Selected ProceduresUNSYMMETRICAL 1,1'-BIDENTATE FERROCENYL LIGANDSIntroductionPalladium-Catalyzed Asymmetric Allylic Substitution ReactionGold or Silver-Catalyzed Asymmetric Aldol ReactionsAsymmetric HydrogenationAsymmetric Cross-Coupling ReactionAsymmetric Heck ReactionMiscellaneousConclusion and PerspectivesExperimental: Selected ProceduresSULFUR- AND SELENIUM-CONTAINING FERROCENYL LIGANDSIntroductionAsymmetric Allylic SubstitutionOther Asymmetric Palladium-Catalyzed ReactionsGold-Catalyzed ReactionsAsymmetric ReductionsAsymmetric 1,2- and 1,4-Nucleophilic AdditionAsymmetric Cycloaddition ReactionsAsymmetric Nucleophilic CatalysisConclusion and PerspectivesExperimental: Selected ProceduresBIFERROCENE LIGANDSIntroductionTrans-Chelating Chiral Bisphosphines: TRAP2,2-Bis(diarylphosphino)-1,1-Biferrocenes: BIFEPMiscellaneous Biferrocene-Based Chiral LigandsConclusionAPPLICATIONS OF AZA- AND PHOSPHAFERROCENES AND RELATED COMPOUNDS IN ASYMMETRIC CATALYSISIntroductionBackground on Aza- and PhosphaferrocenesAzaferrocenes in CatalysisPhosphaferrocenes in CatalysisConclusionsMETALLOCYCLIC FERROCENYL LIGANDSIntroductionAsymmetric Synthesis of Planar Chiral Metallocylic ComplexesStoichiometric Synthetic Applications of Scalemic Planar Chiral Metallocyclic ComplexesAsymmetric Catalysis with Scalemic Planar Chiral Palladocyclic ComplexesConclusionSHOW CASE OF THE MOST EFFECTIVE CHIRAL FERROCENE LIGANDS IN VARIOUS CATALYTIC REACTIONSAsymmetric Allylic Substitution ReactionsAsymmetric Aldol ReactionsAsymmetric Cycloaddition ReactionsAsymmetric HydrogenationPd-Catalyzed Asymmetric Heck ReactionAddition of Organozinc ReagentsAsymmetric Rearrangement of Allylic ImidatesCu-Catalyzed CyclopropanationCoupling Reaction of Vinyl Bromide and 1-Phenylethylzinc ChlorideEnantioselective Intramolecular AminopalladationNickel-Catalyzed Asymmetric Three-Component Coupling of Alkynes, Imines, and Organoboron ReagentsReactions with KetenesRing Opening Reaction

About the author

Li-Xin Dai is professor at the famous Shanghai Institute of Organic Chemistry. He has authored or co-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. His research interests include new synthetic methodology, asymmetric synthesis, and design of novel chiral ligands. He is also a member of Chinese Academy of Sciences, an expert analyst in organic chemistry of Chemtracts and a member of advisory board of Chemical Society Reviews.

Xue-Long Hou is professor at SIOC. The scientific awards professor Hou received include Alexander von Humboldt research fellowship, the Second Class Award of Natural Science of China twice, First Class Award for Advancement of Science and Technology of Shanghai, JSPS Fellowship, and the National Outstanding Youth Fund (2000-2004). His research interests are the design of chiral ligands and their applications in asymmetric catalysis, new synthetic methodology.

Summary

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.

Report

"This book might stand out as a landmark summary that marks the sunset of an intense area of research." ( JACS , 2010)

Product details

• Authors: Li-Xin Dai, Xue-Long Hou
• Assisted by: Li-Xi Dai (Editor), Li-Xin Dai (Editor), Hou (Editor), Hou (Editor), Xue-Long Hou (Editor)
• Publisher: Wiley-VCH
• Languages: English, German
• Product format: Hardback
• Released: 23.12.2009
• EAN: 9783527322800
• ISBN: 978-3-527-32280-0
• No. of pages: 414
• Dimensions: 178 mm x 250 mm x 25 mm
• Weight: 934 g
• Illustrations: 100 SW-Abb.
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, Spektroskopie, ORGANIC CHEMISTRY, Katalyse, chemistry, spectroscopy, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren, Coordination Chemistry, Koordinationschemie, Ferrocen