Chiral Auxiliaries And Ligands In Asymmetric Synthesis

Author : J. Seyden-Penne
Publisher : Wiley-Interscience
ISBN 13 :
Total Pages : 744 pages
Book Rating : 4.43/5 ( download)

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Download or read book Chiral Auxiliaries and Ligands in Asymmetric Synthesis written by J. Seyden-Penne and published by Wiley-Interscience. This book was released on 1995-10-23 with total page 744 pages. Available in PDF, EPUB and Kindle. Book excerpt: Table of Contents Preface Abbreviations Introduction 1 1 Enantiomerically Pure Chiral Auxiliaries 43 2 Chiral Reagents 87 3 Chiral Catalysis and Catalysts Bearing Chiral Ligands 117 4 Asymmetric Deprotonations and Protonations 143 5 Alkylations and Related Reactions 157 6 Additions to C=O and C=N Double Bonds 209 7 Additions to Carbon-Carbon Double Bonds 367 8 Additions to Double Bonds Bearing Heteroatoms. Oxidations of Sulfides and Selenides 503 9 Cycloadditions 513 10 Sigmatropic Rearrangements 593 11 Transition Metal Catalyzed Reactions 619 References 637 Index 707.

Author : Arun A. (Arun Anil) Narine
Publisher : Library and Archives Canada = Bibliothèque et Archives Canada
ISBN 13 :
Total Pages : 590 pages
Book Rating : 4.72/5 ( download)

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Download or read book Design, Synthesis and Evaluation of Chiral Auxiliaries, Ligands and Catalysts for Asymmetric Synthesis [microform] written by Arun A. (Arun Anil) Narine and published by Library and Archives Canada = Bibliothèque et Archives Canada. This book was released on 2004 with total page 590 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Author : G.R. Stephenson
Publisher : Springer Science & Business Media
ISBN 13 : 9400707975
Total Pages : 440 pages
Book Rating : 4.79/5 ( download)

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Download or read book Advanced Asymmetric Synthesis written by G.R. Stephenson and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 440 pages. Available in PDF, EPUB and Kindle. Book excerpt: Asymmetric synthesis is one of the most critical strategic subjects in organic chemistry, and this book describes advanced techniques and their applications to the industrial and laboratory synthesis of important chiral molecules. The international team of highly respected authors provide rigorous and concise reviews of their areas of expertise.

Author : Guo-Qiang Lin
Publisher : John Wiley & Sons
ISBN 13 : 0471465240
Total Pages : 536 pages
Book Rating : 4.49/5 ( download)

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Download or read book Principles and Applications of Asymmetric Synthesis written by Guo-Qiang Lin and published by John Wiley & Sons. This book was released on 2003-05-29 with total page 536 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.

Author : Jacek Wojaczynski
Publisher : John Wiley & Sons
ISBN 13 : 3527834192
Total Pages : 692 pages
Book Rating : 4.98/5 ( download)

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Download or read book Chiral Building Blocks in Asymmetric Synthesis written by Jacek Wojaczynski and published by John Wiley & Sons. This book was released on 2022-08-05 with total page 692 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chiral Building Blocks in Asymmetric Synthesis A comprehensive introduction to the important classes of chiral building blocks Chirality — the asymmetric quality found in certain chemical compounds — plays an essential role in our world: chiral compounds can be found in biology, pharmaceutical compounds, agrochemicals, and fragrances. The stereoselective preparation of these complex molecular constructions constitutes a challenge. To this end, modern asymmetric synthesis utilizes a variety of valuable and efficient reagents employed as chiral auxiliaries, metal complexes and organocatalysts in stereoselective catalysis, and enantiopure reactants termed as chiral building blocks. In Chiral Building Blocks in Asymmetric Synthesis, the achievements in the fields of preparation of and applications of chiral blocks are presented. In doing so, the book comprehensively discusses the important classes of these reactants as the key for the asymmetric synthesis of chiral molecules. As such, it is an indispensable resource about synthetic methods, as well as possible modifications and transformations of important classes of chiral compounds. It also highlights the importance of their use as reactants and auxiliaries in the preparation of more sophisticated molecules or supramolecular systems. In Chiral Building Blocks in Asymmetric Synthesis readers will also find: Organization according to the most important compound classes — e.g. amino acids, BINOL and its derivatives, terpenes, and others — with an emphasis on synthesis and application A focus on the use of chiral building blocks for the preparation of bioactive compounds and supramolecular assemblies Chiral Building Blocks in Asymmetric Synthesis is a useful reference for organic chemists, catalytic chemists, chemists in industry, medicinal chemists, pharmaceutical chemists, and the libraries that support them.

Author : Charles P. Connell
Publisher :
ISBN 13 :
Total Pages : 122 pages
Book Rating : 4.50/5 ( download)

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Download or read book The Importance of Chiral Auxiliaries in Asymmetric Synthesis and Work on a Topologically Chiral Ligand written by Charles P. Connell and published by . This book was released on 1994 with total page 122 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Author : Robert E. Gawley
Publisher : Elsevier
ISBN 13 : 0080914136
Total Pages : 569 pages
Book Rating : 4.38/5 ( download)

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Download or read book Principles of Asymmetric Synthesis written by Robert E. Gawley and published by Elsevier. This book was released on 2012-05-29 with total page 569 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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

Author : David Ager
Publisher : CRC Press
ISBN 13 : 1420027301
Total Pages : 632 pages
Book Rating : 4.03/5 ( download)

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Download or read book Handbook of Chiral Chemicals written by David Ager and published by CRC Press. This book was released on 2005-10-21 with total page 632 pages. Available in PDF, EPUB and Kindle. Book excerpt: As pharmaceutical companies look to develop single enantiomers as drug candidates, chemists are increasingly faced with the problems associated with this subclass of organic synthesis. "The Handbook of Chiral Chemicals, Second Edition" highlights the problems associated with the production of chiral compounds on a commercial scale. The handbook fir

Author : Christine Fee Czauderna
Publisher :
ISBN 13 :
Total Pages : 242 pages
Book Rating : 4.35/5 ( download)

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Download or read book Novel Chiral Wide Bite Angle Ligands for Asymmetric Catalysis written by Christine Fee Czauderna and published by . This book was released on 2013 with total page 242 pages. Available in PDF, EPUB and Kindle. Book excerpt: Achiral wide bite angle ligands have been shown to be highly active and to induce excellent chemo- and regioselectivities in many homogeneously catalyzed reactions. However, only a few examples of chiral wide bite angle ligands are known so far. A diphenyl ether backbone was selected to allow maximum synthetic versatility and potential for a modular approach to design and synthesize such chiral diphosphorus ligands. Three synthetic strategies have been explored in this thesis: i) introduction of chiral substituents in the ligand backbone, ii) the use of P-stereogenic donor atoms and iii) the synthesis of chiral mixed-donor ligands bearing chiral auxiliary groups on the phosphorus atoms. Functionalization of the 3,3'-positions of 2,2'-bis(diphenylphosphino)diphenyl ether by carboxylic acid or ether auxiliaries was achieved via straightforward four-step routes to generate a library of ligands that were tested in various catalytic reactions. In the Pd-catalyzed asymmetric allylic alkylation of l,3-diphenyl-2-propenyl acetate and cyclohexyl-2-enyl acetate with dimethyl malonate the enantioselectivity was found to depend on the size of the chiral auxiliary introduced within the diphenyl ether backbone and its proximity to the phosphorus donor groups and hence to the active metal centre. Two types of mixed donor bidentate diphosphorus ligands based on the diphenylether backbone have been established, i.e. phosphine-phosphite and phosphine-phosphonite derivatives. A small ligand library bearing different chiral auxiliaries was accomplished via straightforward syntheses that enable derivatization of the respective phosphite and phosphonite moieties in the final step. In the Rh-catalysed hydrogenation of several benchmark substrates high conversion and moderate to high enantioselectivities (up to 97% for dimethyl itaconate) were obtained. The enantioselectivity was influenced by the size of the ortho-substituent on the chiral auxiliary group of the phosphite or phosphonite fragment. Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed. Both protocols involved diphenylether as backbone and the chiral ephedrine based precursor (2R[subscript(P)],4S[subscript(C)],5R[subscript(C)])-oxazaphospholidine borane as initial auxiliary to induce chirality at phosphorus. Various novel diphosphines were isolated as highly enantioenriched compounds with dr-ratios up to 95:5.

Author : R.E. Gawley
Publisher : Elsevier
ISBN 13 : 0080514774
Total Pages : 394 pages
Book Rating : 4.72/5 ( download)

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Download or read book Principles of Asymmetric Synthesis written by R.E. Gawley and published by Elsevier. This book was released on 1996-11-21 with total page 394 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.