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

Format:

Book

Author/Creator:

Kolodiazhnyi, Oleg I., author.

Language:

English

Subjects (All):

Organophosphorus compounds.

Organophosphorus compounds--Congresses.

Asymmetric synthesis.

Asymmetric synthesis--Congresses.

Physical Description:

1 online resource (393 p.)

Edition:

1st ed.

Place of Publication:

Weinheim, Germany : Wiley-VCH, 2017.

Summary:

Authored by one of the leading experts in the field, this is the only comprehensive overview of chiral organophosphorus compounds, from asymmetric synthesis to catalysis and pharmacological applications. As such, this unique reference covers the chemical background as well as spectroscopical analysis of phosphorus compounds, and thoroughly describes all the various synthetic strategies for these substances. Metal-, organo- and biocatalyzed reactions for the introduction of phosphorus are explained as are asymmetric oxidation and reduction methods for the preparation of all possible oxidation states of phosphorus. The text also includes industrial applications for these compounds. Of particular interest to chemists working in the field of asymmetric synthesis, as well as to the pharmaceutical industry due to the increasing number of phosphorous-containing drugs.

Contents:

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

Notes:

Description based upon print version of record.

Includes bibliographical references at the end of each chapters and index.

Description based on online resource; title from PDF title page (ebrary, viewed October 7, 2016).

ISBN:

9783527341535

3527341536

9783527341511

352734151X

9783527341542

3527341544

OCLC:

959845761