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Chiral Amine Synthesis

Methods, Developments and Applications

Erschienen am 17.02.2010, 1. Auflage 2010
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Bibliografische Daten
ISBN/EAN: 9783527325092
Sprache: Englisch
Umfang: XXVI, 494 S., 432 s/w Illustr., 92 s/w Tab., 524 I
Format (T/L/B): 2.7 x 24.7 x 17.9 cm
Einband: gebundenes Buch

Beschreibung

Ein international renommiertes Autorenteam stellt Ihnen hier aktuelle Methoden der Synthese chiraler Amine und interessante Anwendungen vor. Mit starkem Praxisbezug!

Produktsicherheitsverordnung

Hersteller:
Wiley-VCH GmbH
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DE 69469 Weinheim


Autorenportrait

Tom Nugent gained his Ph.D. in Organic Chemistry in 1995 from Virginia Tech working with Professor Tomas Hudlicky. From 1996-1997, he completed his postdoctoral studies at the University of Liverpool (Great Britain) with Professor Stanley Roberts.Over the next six years he worked as a process research chemist, first with Catalytica Fine Chemicals / DSM (Mountain View, California, 1998-2000) and then with Pharmacia/Pfizer Corporation (South San Francisco, California, 2001-2003). In 2004 he began his academic career at Jacobs University as Assistant Professor of Organic Chemistry.

Inhalt

PrefaceSTEREOSELECTIVE SYNTHESIS OF ALPHA-BRANCHED AMINES BY NUCLEOPHILIC ADDITION OF UNSTABILIZED CARBANIONS TO IMINESIntroductionOverview of the Methods for the Preparation of IminesChiral Auxiliary-Based ApproachesCatalytic Asymmetric Nucleophilic Addition to Achiral IminesConclusionASYMMETRIC METHODS FOR RADICAL ADDITION TO IMINO COMPOUNDSBackground and IntroductionIntermolecular Radical Addition Chiral N-AcylhydrazonesAsymmetric Catalysis of Radical AdditionClosing RemarksENANTIOSELECTIVE SYNTHESIS OF AMINES BY CHIRAL BRONSTED ACID CATALYSTSIntroductionCarbon-Carbon Bond Forming ReactionsCarbon-Hydrogen Bond Forming ReactionsCarbon-Heteroatom Bond Forming ReactionsConclusionREDUCTION OF IMINES WITH TRICHLOROSILANE CATALYZED BY CHIRAL LEWIS BASESIntroductionFormamides as Lewis-Basic Organocatalysts in Hydrosilylation of IminesOther Amides as Organocatalysts in Hydrosilylation of IminesSulfinamides as Organocatalysts in Hydrosilylation of IminesSupported Organocatalysts in Hydrosilylation of IminesMechanistic ConsiderationsSynthetic ApplicationsConclusionsTypical Procedures for the Catalytic Hydrosilylation of IminesCATALYTIC, ENANTIOSELECTIVE; VINYLOGOUS MANNICH REACTIONSIntroductionVinylogous Mukaiyama-Mannich Reactions of Silyl DienolatesDirect Vinylogous Mannich Reactions of Unmodified SubstratesMiscellaneousConclusionCHIRAL AMINES FROM TRANSITION-METAL-MEDIATED HYDROGENATION AND TRANSFER HYDROGENATIONScope and Related PublicationsChiral Amines with a Disubstituted Nitrogen Atom, HNR*R1Chiral Amines with Trisubstituted Nitrogen, NR*R1R2ConclusionASYMMETRIC REDUCTIVE AMINATIONIntroductionTransition Metal-Mediated Homogenous Reductive AminationEnantioselective Organocatalytic Reductive AminationDiastereoselective Reductive AminationConclusionsENANTIOSELECTIVE HYDROGENATION OF ENAMINES WITH MONODENTATE PHOSPHORUS LIGANDSIntroductionAsymmetric Hydrogenation of EnamidesAsymmetric Hydrogenation of N,N-Dialkyl EnaminesConclusion and OutlookBIDENTATE LIGANDS FOR ENANTIOSELECTIVE ENAMIDE REDUCTIONIntroductionCatalytic Enantioselective Hydrogenation of EnamidesConclusionsENANTIOSELECTIVE REDUCTION OF NITROGEN-BASED HETEROAROMATIC COMPOUNDSAsymmetric Hydrogenation of QuinolinesAsymmetric Hydrogenation of IsoquinolinesAsymmetric Hydrogenation of PyrrolesAsymmetric Hydrogenation of QuinoxalinesAsymmetric Hydrogenation of Pyridine DerivativesSummary and OutlookASYMMETRIC HYDROAMINATIONIntroduction: Synthesis of Amines via HydroaminationHydroamination of Simple, Nonactivated AlkenesHydroamination of Dienes, Allenes, and AlkynesHydroamination with Enantiomerical Pure AminesSynthesis of Chiral Amines via Tandem Hydroamination/HydrosilylationConclusionsExperimental SectionENANTIOSELECTIVE C-H AMINATIONIntroductionBackgroundRacemic C-H AminationSubstrate-Controlled Chiral Amine Synthesis via C-H AminationEnantioselective C-H Amination of Achiral SubstratesConclusionCHIRAL AMINES DERIVED FROM ASYMMETRIC AZA-MORITA-BAYLIS-HILLMAN REACTIONIntroductionRecent Mechanistic InsightsAsymmetric Aza-MBH ReactionChiral Auxiliary-Induced Diastereoselective Aza-MBH ReactionChiral Teriary Amine CatalystsChiral Phosphine CatalystsChiral Bifunctional N-Heterocyclic CarbenesChiral Ionic Liquids as Reaction MediumAza-MBH-Type Reaction to Obtain Chiral AminesStrategies for the Removal of Protecting GroupsSelected Typical Experimental ProceduresSummary and OutlookBIOCATALYTIC ROUTES TO NONRACEMIC CHIRAL AMINESIntroductionKinetic Resolution of Racemic AminesDKR and Deracemization of AminesAsymmetric Synthesis of Amines Using TransaminasesConclusions and Future Perspectives

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