Principles of Asymmetric Synthesis

Principles of Asymmetric Synthesis

The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations. Authoritative glossary to aid understanding of stereochemical terminology Explanations of the key factors influencing stereoselectivity with numerous examples, organized by reaction type A handy reference guide to the literature of asymmetric synthesis for practitioners in the field


Author
Publisher Elsevier
Release Date
ISBN 0080448607
Pages 555 pages
Principles of Asymmetric Synthesis
Language: en
Pages: 555
Authors: Robert E. Gawley
Categories: Science
Type: BOOK - Published: 2012 - Publisher: Elsevier

The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtaine
Principles of Asymmetric Synthesis
Language: en
Pages: 394
Authors: R.E. Gawley
Categories: Science
Type: BOOK - Published: 1996-11-21 - Publisher: Elsevier

The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtaine
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Language: en
Pages: 536
Authors: Guo-Qiang Lin
Categories: Science
Type: BOOK - Published: 2003-05-29 - Publisher: John Wiley & Sons

Asymmetric synthesis remains a challenge to practicing scientistsas the need for enantiomerically pure or enriched compoundscontinues to increase. Over the last
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Language: en
Pages: 189
Authors: Y. Vatsala
Categories: Asymmetric synthesis
Type: BOOK - Published: 2015 - Publisher:

The Principles of Asymmetric Synthesis
Language: en
Pages: 26
Authors: Joseph Fredric Haskins
Categories: Asymmetric synthesis
Type: BOOK - Published: 1920 - Publisher:

Fundamentals of Asymmetric Catalysis
Language: en
Pages: 692
Authors: Patrick J. Walsh
Categories: Science
Type: BOOK - Published: 2009-01-02 - Publisher: University Science Books

This book describes the essential aspects of enantioselective catalysis in a clear, logical fashion, with chapters organized by concept rather than by reaction
Asymmetric Synthesis
Language: en
Pages: 237
Authors: Garry Procter
Categories: Science
Type: BOOK - Published: 1996 - Publisher: Oxford University Press on Demand

This book covers a wide range of reactions which are of importance in the asymmetric synthesis of organic compounds. The principles of asymmetric additions to c
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Language: en
Pages: 388
Authors: Ari M. P. Koskinen
Categories: Science
Type: BOOK - Published: 2022-11-14 - Publisher: John Wiley & Sons

Fully updated textbook learning resource covering the concept of using natural product chemistry for strategies in asymmetric synthesis The third edition of Asy
Dynamic Stereochemistry of Chiral Compounds
Language: en
Pages: 534
Authors: Christian Wolf
Categories: Science
Type: BOOK - Published: 2008 - Publisher: Royal Society of Chemistry

A comprehensive overview of fundamental concepts of asymmetric synthesis along with in-depth discussion. Recent developments that address important synthetic ch
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Language: en
Pages: 393
Authors: Vittorio Caprio
Categories: Science
Type: BOOK - Published: 2009-03-09 - Publisher: John Wiley & Sons

Written from a synthetic organic chemistry perspective, this is a highly practical and relevant text for undergraduates, postgraduates and industrial organic ch