Stereoselective synthesis [[electronic resource] ] : a practical approach / / Mihály Nógrádi ; foreword by A.I. Meyers

• Record Nr.: UNISA996202135403316
• Autore: Nógrádi M
• Pubbl/distr/stampa: Weinheim ; ; New York, : VCH, 1995
• ISBN: 1-281-75874-4; 9786611758745; 3-527-61569-5; 3-527-61568-7
• Edizione: [2nd, thoroughly rev. and updated ed.]
• Descrizione fisica: 1 online resource (390 p.)
• Disciplina: 541.223; 541.39
• Soggetti: Stereochemistry; Stereoisomers; Organic compounds - Synthesis
• 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 (p. [315]-358) and index.
• Nota di contenuto: Stereoselective Synthesis; Contents; List of Symbols and Abbreviations; Introduction; 1 General Concepts of Stereoselective Synthesis; 1.1 Principles of Differentiating Molecules; 1.2 Characterization of Stereoisomers. Conformation and Configuration; 1.3 Intramolecular Symmetry. Topicity and Prochirality; 1.4 Selectivity in Chemistry; 1.4.1 Substrate Selectivity; 1.4.1.1 Substrate Diastereoselectivity (Diastereomer Selectivity); 1.4.1.2 Substrate Enantioselectivity (Enantiomer Selectivity). Kinetic Resolution; 1.4.2 Product Selectivity; 1.4.2.1 Formation of Stereoisomers; 1.4.2.2 Conditions Necessary for Stereoselectivity1.4.2.3 Concept of Stereodifferentiation; 1.4.2.4 Methods for Inducing Stereoselectivity; 1.4.3 Stereoselective Synthetic Strategies; 1.4.3.1 Enantioconvergent Synthesis; 1.4.3.2 Selective Preparation of Both Enantiomers from a Single Substrate; 1.5 Kinetics and Thermodynamics of Stereoselective Reactions; 2 Stereoselective Catalytic Reductions; 2.1 Stereoselective Homogeneous Hydrogenations with Rhodium-, Ruthenium- and Iridium-Phosphine Catalysts; 2.1.1 Hydrogenation of Olefinic Bonds; ; 2.1.1.1 Chiral Phosphorus Containing Ligands; 2.1.2 Enantioselective Catalytic Hydrogenation of Ketones and Imines2.1.3 Diastereoselective Hydrogenations in Homogeneous Phase; 2.2 Catalytic Hydrosilylation; 2.3 Heterogeneous Stereoselective Catalytic Hydrogenations; 2.3.1 Enantioselective Heterogeneous Catalytic Hydrogenations; 2.3.2 Diastereoselective Heterogeneous Catalytic Hydrogenations; 3 Stereoselective Non-Catalytic Reductions; 3.1 Enantioselective Reductions; 3.1.1 Chiral Lithium Aluminum Hydrides; 3.1.1.1 Reduction of Carbonyl Groups; 3.1.1.2 Reduction of C=N and C=C Bonds; 3.1.2 Chirally Modified Hydridoborates; 3.1.3 Chiral Boranes and Boronates3.1.4 Enantioselective Reductions with Hydride Transfer from Carbon; 3.1.4.1 Chiral Trialkylboranes; 3.1.4.2 Chiral Metal Alkyls; 3.1.4.3 Chiral Metal Alkoxides; 3.1.4.4 Chiral 1 ,4-Dihydropyridines; 3.1.5 Correlation of Substrate Constitution and Enantioselectivity; 3.2 Diastereoselective Reductions of Carbonyl Groups; 3.2.1 Stereochemistry of Diastereoselective Ketone Reductions; 3.2.2 Practical Aspects of Diastereoselective Ketone Reductions; 4 Stereoselective Oxidations; 4.1 Enantioselective Oxidations; 4.1.1 Epoxidation with Chiral Oxidants; 4.1.2 Oxidations in the Presence of Chiral Catalysts4.2 Diastereoselective Oxidations; 4.2.1 Diastereoselective Epoxidation; 4.2.2 Various Diastereoselective Oxidations; 5 Stereoselective Carbon-Carbon Bond Forming Reactions by Nucleophilic Addition to Carbonyl Groups; 5.1 Addition of Simple Nucleophiles to Carbonyl Compounds; 5.1.1 Enantioselective Additions; 5.1.2 Diastereoselective Additions; 5.1.3 Additions to C=N Bonds; 5.2 Additions Involving Allylmetal and Allylboron Compounds; 5.2.1 General Aspects of Allylmetal Addition; 5.2.2 Addition of Allylboron Compounds; 5.2.3 Addition of Allyltitanium Compounds
• Sommario/riassunto: The state-of-the-art in stereoselective synthesis!Thoroughly revised and updated, this enlarged second edition offers a plethora of valuable information on methods and reagents in stereoselective synthesis. Methods have been selected for high efficiency and selectivity; mechanistic aspects are treated succinctly, with a strong emphasis on practical applications. For this new edition, material has been added on* homogeneous diastereoselective hydrogenations* enantioselective oxidations* novel, efficient chiral auxiliariesMuch of the information given is presented in figu