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Principles Of Asymmetric Synthesis

Author: R.E. Gawley
Publisher: Elsevier
ISBN: 9780080514772
Size: 14.57 MB
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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 Of Asymmetric Synthesis

Author: Robert E. Gawley
Publisher: Elsevier
ISBN: 0080914136
Size: 40.67 MB
Format: PDF
View: 5279
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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

Author: Y. Vatsala
Publisher:
ISBN: 9781781830130
Size: 64.40 MB
Format: PDF
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Deals with stereochemistry of specialised topics. This book provides a comprehensive account of concepts of Asymmetric Synthesis. It is based on three important principles: concepts and terminology used in asymmetric synthesis, the four types of asymmetric synthesis, and applications of asymmetric synthesis.

Principles And Applications Of Asymmetric Synthesis

Author: Guo-Qiang Lin
Publisher: John Wiley & Sons
ISBN: 0471465240
Size: 36.53 MB
Format: PDF
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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.

Asymmetric Synthesis

Author: Alan Aitken
Publisher: CRC Press
ISBN: 9780751401905
Size: 60.43 MB
Format: PDF, Kindle
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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.

Dynamic Stereochemistry Of Chiral Compounds

Author: Christian Wolf
Publisher: Royal Society of Chemistry
ISBN: 0854042466
Size: 68.59 MB
Format: PDF, Docs
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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.

Asymmetric Catalysis In Organic Synthesis

Author: Ryoji Noyori
Publisher: Wiley-Interscience
ISBN:
Size: 10.34 MB
Format: PDF, Docs
View: 2004
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Deals with basic principles of asymmetric catalysis focusing on its synthetic significance. Covers homogeneous asymmetric hydrogenation, asymmetric catalysis via chiral metal complexes, heterogeneous catalysis and non-organometallic catalysis. The collection of a range of stereoselective reactions illustrate various strategies and methodologies as well as their general utility.

Asymmetric Synthesis Of Natural Products

Author: Ari M. P. Koskinen
Publisher: John Wiley & Sons
ISBN: 1118347331
Size: 15.77 MB
Format: PDF
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Asymmetric Synthesis of Natural Products, 2nd Edition introduces students to this rapidly growing field of organic chemistry. The initial chapters present the foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions. This is followed by chapters on each of the major individual classes of natural products; their structures, biosynthesis and interrelationships as well as examples of asymmetric syntheses and the practical value of these compounds. Natural product classes covered include carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, polyketides, isoprenoids, shikamic acid derivatives and alkaloids. For this second edition the text has been thoroughly updated and expanded, and includes new discussions and examples covering atom and redox economies, practical aspects and environmental awareness. Organocatalysis has emerged completely in the last ten years, and has been fully integrated into this new edition.

Chiral Auxiliaries And Ligands In Asymmetric Synthesis

Author: J. Seyden-Penne
Publisher: Wiley-Interscience
ISBN: 9780471116073
Size: 15.67 MB
Format: PDF, Kindle
View: 1991
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Chiral molecules are molecules that come in left and right handed forms - they are mirror images of each other and behave differently in the body. This important book show chemists how to prepare chiral molecules to get the desired form. Presents an overview of the chiral auxiliaries, reagents and catalysts used in synthesis. Covers underlying principles.

Asymmetric Synthesis

Author: Garry Procter
Publisher: Oxford University Press on Demand
ISBN: 9780198557258
Size: 40.31 MB
Format: PDF, ePub
View: 1687
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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 carbonyls, enolate alkylation, aldol reactions, additions to C-C double bonds, reduction and oxidation, rearrangements, and hydrolysis/ esterification reactions are covered, and selected examples used to illustrated the various topics. Numerous references to original literature should be of ues to organic chemists interested in the area of asymmetric synthesis.