Asymmetric synthesis in organophosphorus chemistry : synthetic methods, catalysis, and applications / / Oleg I. Kolodiazhnyi

• Record Nr.: UNINA9910814764703321
• Autore: Kolodiazhnyi Oleg I.
• Pubbl/distr/stampa: Weinheim, Germany : , : Wiley-VCH, , 2017; ©2017
• ISBN: 3-527-34153-6; 3-527-34151-X; 3-527-34154-4
• Descrizione fisica: 1 online resource (393 p.)
• Disciplina: 547.07
• Soggetti: Organophosphorus compounds; Asymmetric 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 at the end of each chapters and index.
• Nota di contenuto: Cover; Title Page; Copyright; Dedication; Contents; Preface; Abbreviations; Chapter 1 Fundamentals of the Stereochemistry of Organophosphorus Compounds; 1.1 Historical Background; 1.2 Some Common Definitions in Stereochemistry; 1.3 Determination of Enantiomer Composition; 1.3.1 Method of Nuclear Magnetic Resonance; 1.3.1.1 Chiral Solvating Agents; 1.3.1.2 Complexes of Metals (Shift Reagents); 1.3.1.3 Chiral Derivatizing Agents for NMR; 1.3.2 Chromatographic Methods of Analysis; 1.3.2.1 Gas Chromatography; 1.3.2.2 Liquid Chromatography; 1.4 Determination of the Absolute Configuration; 1.4.1 X-ray Crystal Analysis1.4.2 Method of Chemical Correlation; 1.4.3 The Assignment of Absolute Configuration by NMR; 1.5 Asymmetric Induction and Stereochemistry; 1.5.1 Asymmetric Induction; 1.5.2 Asymmetric Synthesis; 1.5.3 Asymmetric Transformation; 1.5.4 An Enantioselective Reaction; 1.5.5 Enantioselective Synthesis; 1.6 Summary; References; Chapter 2 Asymmetric Synthesis of P-Chirogenic Phosphorus Compounds; 2.1 Introduction; 2.2 Low-Coordinated Phosphorus Compounds; 2.3 Trivalent Tricoordinated Phosphorus Compounds; 2.3.1 Configuration Stability of P(III)-Compounds; 2.3.2 Asymmetric Nucleophilic Substitution at P (III)2.3.2.1 Secondary Alcohols as Chiral Auxiliaries; 2.3.2.2 Optically Active Amines as Chiral Auxiliaries; 2.3.2.3 Ephedrine as Inductor of Chirality at P(III); 2.3.3 Asymmetric Oxidation of P(III) Compounds; 2.3.4 Asymmetric Electrophilic Substitution at P(III); 2.3.4.1 Asymmetric Michaelis-Arbuzov Reaction; 2.4 Pentavalent P(IV)-Phosphorus Compounds; 2.4.1 Introduction; 2.4.2 Nucleophilic Substitution Reactions; 2.4.2.1 Nucleophilic Substitution at P(IV) with Chiral Alcohol; 2.4.2.2 Nucleophilic Substitution at P(IV) with Chiral Amines; 2.5 Chiral P(V) and P(VI) Phosphorus Compounds2.6 Summary; References; Chapter 3 Phosphorus Compounds with Chiral Side-Chain Centers; 3.1 Introduction; 3.2 Asymmetric Induction in Side Chains; 3.2.1 Transfer of Chirality from Phosphorus to Other Centers; 3.2.1.1 Chiral Phosphorus-Stabilized Anions; 3.2.1.2 1,2-Asymmetric Induction; 3.2.1.3 1,4-Asymmetric Induction; 3.3 Enantioselective Olefination; 3.4 Stereoselective Addition of Phosphorous Nucleophiles to C=X Bonds; 3.4.1 Phospha-Aldol Reaction; 3.4.2 Phospha-Mannich Reaction; 3.4.3 Phospha-Michael Reaction; 3.5 Asymmetric Reduction; 3.6 Asymmetric Oxidation3.7 C-Modification; 3.8 Asymmetric Cycloaddition; 3.9 Multiple Stereoselectivity; 3.10 Summary; References; Chapter 4 Asymmetric Catalysis with Metal Complexes; 4.1 Introduction; 4.2 Asymmetric Catalytic Hydrogenation and Other Reactions of Reduction; 4.2.1 Hydrogenation of C=C Phosphorus Compounds; 4.2.2 Hydrogenation of C=O Phosphorus Compounds; 4.3 Asymmetric Reduction and Oxidation; 4.3.1 Reduction of C=O, C=N, and C=C bonds; 4.3.2 Asymmetric Oxidation; 4.4 Electrophilic Asymmetric Catalysis; 4.4.1 Catalytic Electrophilic Substitution at the Phosphorus Atom; 4.4.1.1 Alkylation and Arylation of P(III) Compounds