Principles of Asymmetric Synthesis

Principles of Asymmetric Synthesis
Author: R.E. Gawley,J. Aubé
Publsiher: Elsevier
Total Pages: 395
Release: 1996-11-21
Genre: Science
ISBN: 9780080514772

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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.

Principles and Applications of Asymmetric Synthesis

Principles and Applications of Asymmetric Synthesis
Author: Guo-Qiang Lin,Yue-Ming Li,Albert S. C. Chan
Publsiher: John Wiley & Sons
Total Pages: 536
Release: 2003-05-29
Genre: Science
ISBN: 9780471465249

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Asymmetric synthesis remains a challenge to practicing scientistsas the need for enantiomerically pure or enriched compoundscontinues to increase. Over the last decade, a large amount ofliterature has been published in this field. Principles andApplications of Asymmetric Synthesis consolidates and evaluates themost useful methodologies into a one-volume resource for theconvenience of practicing scientists and students. Authored by internationally renowned scientists in the field, thisreliable reference covers more than 450 reactions and includesimportant stoichiometric as well as catalytic asymmetric reactions.The first chapter reviews the basic principles, commonnomenclature, and analytical methods, and the remainder of the bookis organized according to reaction type. The text examines suchtopics as: Carbon-carbon bond formations involving carbonyls, enamines,imines, and enolates Asymmetric C-O bond formations including epoxidation,dihydroxylation, and aminohydroxylation Asymmetric synthesis using the Diels-Alder reaction and othercyclizations Applications to the total synthesis of natural products Use of enzymes in asymmetric synthesis Practicing chemists in the pharmaceutical, fine chemical, andagricultural professions as well as graduate students will findthat Principles and Applications of Asymmetric Synthesis affordscomprehensive and current coverage.

Principles of Asymmetric Synthesis

Principles of Asymmetric Synthesis
Author: Robert E. Gawley,Jeffrey Aube
Publsiher: Elsevier
Total Pages: 569
Release: 2012-05-29
Genre: Science
ISBN: 9780080914138

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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, this book presents a detailed analysis of the factors that govern stereoselectivity in organic reactions. After an explanation of the basic physical-organic principles governing stereoselective reactions, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Practical Aspects of Asymmetric Synthesis" provides a critical overview of the most common methods for the preparation of enantiomerically pure compounds, techniques for analysis of stereoisomers using chromatographic, spectroscopic, and chiroptical methods. The authors then present an overview of the most important methods in contemporary asymmetric synthesis organized by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions, one chapter on reductions, and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). This organization allows the reader to compare the leading methods for asymmetric synthesis in an appropriate context. A highlight of the book is the presentation and discussion of transition states at the current level of understanding, for important reaction types. In addition, extensive tables of examples are used to give the reader an appreciation for the scope of each reaction. Finally, leading references are provided to natural product synthesis that has been accomplished using a given reaction as a key step. - 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

Asymmetric Synthesis

Asymmetric Synthesis
Author: Alan Aitken,S. N. Kilenyi
Publsiher: CRC Press
Total Pages: 256
Release: 1992-12-30
Genre: Science
ISBN: 0751401900

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Asymmetric synthesis is one of the most important areas of research and development in synthetic organic chemistry, and has wide-ranging industrial applications. This introduction to the subject covers chirality, nomenclature and analytical methods of resolution. The main body of the text describes the principal methods available to the organic chemist wishing to synthesize chiral compounds. Case studies are included, and reference sections allow access to the relevant review and research literature. This book is written for organic chemists at postgraduate and advanced undergraduate level.

Asymmetric Synthesis

Asymmetric Synthesis
Author: Y. Vatsala
Publsiher: Unknown
Total Pages: 189
Release: 2015
Genre: Asymmetric synthesis
ISBN: 1781830894

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Dynamic Stereochemistry of Chiral Compounds

Dynamic Stereochemistry of Chiral Compounds
Author: Christian Wolf
Publsiher: Royal Society of Chemistry
Total Pages: 534
Release: 2008
Genre: Education
ISBN: 9780854042463

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A comprehensive overview of fundamental concepts of asymmetric synthesis along with in-depth discussion. Recent developments that address important synthetic challenges are presented and highlighted with hundreds of examples.

Fundamentals of Asymmetric Catalysis

Fundamentals of Asymmetric Catalysis
Author: Patrick J. Walsh,Marisa C. Kozlowski
Publsiher: University Science Books
Total Pages: 692
Release: 2009-01-02
Genre: Science
ISBN: 1891389548

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This work describes the essential aspects of enantioselective catalysis, with chapters organised by concept rather than by reaction type. Each concept is supported by examples to give the reader broad exposure to a wide range of catalysts, reactions and reaction mechanisms.

Stereochemistry and Organic Reactions

Stereochemistry and Organic Reactions
Author: Dipak Kumar Mandal
Publsiher: Academic Press
Total Pages: 640
Release: 2021-04-21
Genre: Science
ISBN: 9780128240939

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Stereochemistry and Organic Reactions: Conformation, Configuration, Stereoelectronic Effects and Asymmetric Synthesis provides coverage on the stereochemistry of reactions of all mechanistic types, ranging from ionic, pericyclic and transition metal-catalyzed to radical and photochemical. Chapters cover acyclic molecules, cyclic molecules, the stereochemistry of organic reactions, the perturbation molecular orbital theory for the origin of stereoelectronic effects, and an introduction to the principles of stereoselectivity and hierarchical levels of asymmetric synthesis. Each chapter includes problems that reinforce main themes, making it valuable to students, teachers and researchers working in organic, biological and medicinal chemistry, as well as biologists, pharmacologists, polymer chemists and chemists. - Presents a holistic and unified approach to stereochemical understanding and predictions, covering reactions of all mechanistic classes - Includes two background chapters on perturbation theory and stereoselective principles, along with asymmetric designs - Features novel rules and mnemonics to delineate product stereochemistry - Includes up-to-date coverage with over 1300 selective references