Chiral amine synthesis [[electronic resource] ] : methods, developments and applications / / edited by Thomas C. Nugent

• Record Nr.: UNINA9910829885503321
• Pubbl/distr/stampa: Weinheim, : Wiley-VCH Verlag GmbH & Co., 2010
• ISBN: 1-282-46293-8; 9786612462931; 3-527-62954-8; 3-527-62955-6
• Descrizione fisica: 1 online resource (522 p.)
• Classificazione: 540
• Disciplina: 547.042
• Soggetti: Chirality; Amines; Handbook; handbooks.; Reference works; Handbooks and manuals; Handbooks and manuals.; Reference works.; Guides et manuels.; Ouvrages de référence
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: Chiral Amine Synthesis; Foreword; Contents; Preface; List of Contributors; 1 Stereoselective Synthesis of a-Branched Amines by Nucleophilic Addition of Unstabilized Carbanions to Imines; 1.1 Introduction; 1.2 Overview of the Methods for the Preparation of Imines; 1.2.1 N-Aryl and N-Alkyl Imines and Hydrazones; 1.2.2 N-Sulfinyl Imines; 1.2.3 N-Sulfonyl Imines; 1.2.4 N-Phosphinoyl Imines; 1.2.5 N-Acyl and N-Carbamoyl Imines; 1.3 Chiral Auxiliary-Based Approaches; 1.3.1 Imines Derived from Chiral Aldehydes; 1.3.2 Imines Bearing a Chiral Protecting/Activating Group; 1.4 Catalytic Asymmetric Nucleophilic Addition to Achiral Imines1.4.1 ; Catalytic Asymmetric Addition of sp3 Hybridized Carbanions; 1.4.1.1 Copper-Catalyzed Dialkylzinc Additions; 1.4.1.2 Zinc Alkoxide-Catalyzed Dialkylzinc Additions; 1.4.1.3 Early Transition Metal (Zr, Hf)-Catalyzed Dialkylzinc Additions; 1.4.1.4 Rhodium-Catalyzed Dialkylzinc Addition Reactions; 1.4.2 Catalytic Asymmetric Allylation of Imines; 1.4.3 Catalytic Asymmetric Addition of sp2 Hybridized Carbanions; 1.4.3.1 Catalytic Asymmetric Vinylation; 1.4.3.2 Catalytic Asymmetric Arylation; 1.4.3.2.1 Amino Alcohol-Catalyzed Addition of Organozinc Reagents1.4.3.2.2 Rhodium Phosphine-Catalyzed Arylation of Imines; 1.4.3.2.3 Rhodium Diene-Catalyzed Arylation of Imines; 1.4.4 Catalytic Asymmetric Addition of sp Hybridized Carbanions; 1.5 Conclusion; References; 2 Asymmetric Methods for Radical Addition to Imino Compounds; 2.1 Background and Introduction; 2.2 Intermolecular Radical Addition Chiral N-Acylhydrazones; 2.2.1 Design of Chiral N-Acylhydrazones; 2.2.2 Preparation of Chiral N-Acylhydrazones; 2.2.3 Tin-Mediated Addition of Secondary and Tertiary Radicals; 2.2.4 Tin-Free Radical Addition2.2.5 Manganese-Mediated Radical Addition; 2.2.6 Manganese-Mediated Coupling with Multifunctional Precursors; 2.2.6.1 Hybrid Radical-Ionic Annulation; 2.2.6.2 Precursors Containing Hydroxyl or Protected Hydroxyl Groups; 2.2.6.3 Ester-Containing N-Acylhydrazones; 2.2.6.4 Additions to Ketone Hydrazones; 2.3 Asymmetric Catalysis of Radical Addition; 2.4 Closing Remarks; References; 3 Enantioselective Synthesis of Amines by Chiral Brønsted Acid Catalysts; 3.1 Introduction; 3.2 Carbon-Carbon Bond Forming Reactions; 3.2.1 Mannich and Related Reactions; 3.2.1.1 Mannich Reaction3.2.1.2 Nucleophilic Addition of Diazoacetates to Aldimine; 3.2.1.3 Vinylogous Mannich Reaction; 3.2.1.4 Aza-Petasis-Ferrier Rearrangement; 3.2.2 One-Carbon Homologation Reactions; 3.2.2.1 Strecker Reaction; 3.2.2.2 Aza-Henry Reaction; 3.2.2.3 Imino-Azaenamine Reaction; 3.2.3 Friedel-Crafts and Related Reactions; 3.2.3.1 Friedel-Crafts Reaction via Activation of Aldimines; 3.2.3.2 Friedel-Crafts Reaction via Activation of Electron-Rich Alkenes; 3.2.3.3 Pictet-Spengler Reaction; 3.2.4 Cycloaddition Reactions; 3.2.4.1 Hetero-Diels-Alder Reaction of Aldimines with Siloxydienes
• Sommario/riassunto: This first comprehensive presentation of this hot and important topic compiles the most up-to-date methods for chiral amine synthesis. The international list of authors reads like a ""Who's Who"" of the subject, providing a large array of highly practical information concentrated into the useful and essential methods.Following an introductory chapter devoted to helping readers quickly determine which strategies to choose for their investigation, this handbook and ready reference focuses on the examination of methods that are reliable and simultaneously efficient for the synthesis of struc