Enantioselective Synthesis of Beta-Amino Acids
Enantioselective Synthesis of Beta-Amino Acids

Author: Eusebio Juaristi

Publisher: John Wiley & Sons

Published: 2005-05-06

Total Pages: 658

ISBN-13: 0471698474

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Covers all facets of the synthesis of ß-amino acids As evidenced by an exponential increase in the literature published on the subject, interest in ß-amino acids has grown over the past several years. With major pharmaceutical applications, these amino acids are now studied across multiple lines of research, including combinatorial chemistry, medicinal chemistry, molecular design, proteomics, and others. This Second Edition of Enantioselective Synthesis of ß-Amino Acids updates reviews included in the First Edition while also covering new developments since its publication. The book presents detailed discussions of the most important methods for the synthesis of ß-amino acids. In most cases, the lead chemist who originally developed a method provides an authoritative description of it. In addition, Enantioselective Synthesis of ß-Amino Acids, Second Edition: * Features introductory overviews on the structural types of relevant ß-amino acid targets and salient ß-amino acids present in natural products * Dedicates several chapters to advances in the synthesis of oligomers from ß-amino acids * Includes general and practical procedures for the preparation of ß-amino acids in each chapter * Discusses the most important methods that have been recently developed for the asymmetric synthesis of cyclic and open-chain ß-amino acids * Includes a report on the preparation of libraries of enantiopure ß-amino acids using combinatorial approaches The only book of its kind available today, Enantioselective Synthesis of ß-Amino Acids, Second Edition offers upper-level students and professionals an essential resource for pharmaceutical development, medicinal chemistry, and biochemistry.

Synthesis of Optically Active [alpha]-amino Acids
Synthesis of Optically Active [alpha]-amino Acids

Author: Robert Michael Williams

Publisher: Pergamon

Published: 1989

Total Pages: 436

ISBN-13:

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The purpose of this book is to review and critically evaluate the best new methods to synthesize alpha-amino acids in optically active form. There is so much new literature on amino acid synthesis that the experimentalist will undoubtedly have difficulty in selecting the most appropriate methodology for constructing the amino acid of immediate interest. This book is a guide for steering the scientist through the maze of existing reports on the subject and contains the most up-to-date critical reviews of methods of asymmetric synthesis of amino acids. In areas that are relatively new conceptually and less studied experimentally, an effort has been made to review the most salient works with an eye towards future development. Over 330 schemes and figures are presented with references for rapid visual retrieval of information. The book will be of great value to academic and industrial organic research chemists, especially those concerned with medicinal and agricultural chemistry, as well as to graduate and post graduate students, biochemists and biologists.

Organo-catalytic Strategies Towards Alpha, Alpha - Disubstituted Amino Acid Derivatives
Organo-catalytic Strategies Towards Alpha, Alpha - Disubstituted Amino Acid Derivatives

Author: Henning Vogt

Publisher:

Published: 2006

Total Pages: 195

ISBN-13: 9783832513825

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The class of non-proteinogenic a,a u2011disubstituted amino acids and their derivatives is of high interest to biochemical and pharmacological research. This predicates on their ability to alter certain chemical and physicochemical properties of peptides and related structures. Moreover, the close structural relatedness to biologically relevant endogenous amino acid derivatives qualifies them in many cases to act as enzyme inhibitors or receptor antagonists.In the present study, the development of new strategies towards the synthesis of N u2011protected a,a u2011disubstituted amino aldehydes and their derivatives is demonstrated. Starting from ketones, a,a u2011disubstituted aldehydes were prepared in two or three steps. These aldehydes were subjected to stereoselective organo-catalysed a u2011amination reactions. The transfer of a procedure known for the a u2011amination of a u2011unbranched aldehydes with azodicarboxylates to racemic a u2011branched aldehydes delivered N u2011protected aminoaldehydes in up to 87 % yield and 86 % ee. The conversion of the amination products to the corresponding N u2011protected 4,4 u2011disubstituted oxazolidinones was accomplished, after in situ-reduction, in two additional steps.In addition to this method, a new strategy was devised using sulfonyl azides as aminating agent to deliver a u2011sulfamidated a,a u2011disubstituted aldehydes in up to 55 % yield and 86 % ee. A mechanism was proposed, which differs fundamentally from the mechanistic model usually ascribed to enamine catalysis. The transformation of the sulfamidation product into the free amino acid was accomplished in two steps.Since the two concepts follow different mechanistic routes, different enantiomers of N u2011protected, a,a u2011disubstituted aminoaldehydes are accessible by one catalyst. All reactions involved in the latter approach are free of transition metals. Therefore, the presented strategy could prove to be especially useful for medicinal chemistry.

Catalytic Asymmetric Synthesis
Catalytic Asymmetric Synthesis

Author: Takahiko Akiyama

Publisher: John Wiley & Sons

Published: 2022-05-27

Total Pages: 798

ISBN-13: 1119736412

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Catalytic Asymmetric Synthesis Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include: Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis C–H bond functionalization reactions Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions Axially chiral compounds Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.

Asymmetric Synthesis of Non-Proteinogenic Amino Acids
Asymmetric Synthesis of Non-Proteinogenic Amino Acids

Author: Ashot S. Saghyan

Publisher: John Wiley & Sons

Published: 2016-08-08

Total Pages: 376

ISBN-13: 352780448X

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Authored by two internationally recognized experts with an excellent track record, this much-needed reference summarizes latest research in the rapidly developing field of stereoselective synthesis of enantiomerically enriched amino acids, particularly of non-proteinogenic origin. It highlights several different catalytic and stoichiometric asymmetric methods for their synthesis and also provides information on origin, biological properties, different synthetic strategies and important applications in medicine and pharmacology. Essential reading for synthetic chemists working in the field of asymmetric synthesis, natural products and peptide synthesis, stereochemistry, medicinal chemistry, biochemistry, pharmacology, and biotechnology.