Methods of Non-Alpha-Amino Acid Synthesis

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This work provides a comprehensive overview of, and the most common and useful methods for, the synthesis of non-alpha-amino acids, particularly amino acids that are key synthetic intermediates or important compounds in their own right. Attention is paid to acyclic amino acids C3-C10 including amino alkanoic carboxylic acids, aminoalkenoic acids and aminoalkynoic acids.
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More About This Book

Overview

This work provides a comprehensive overview of, and the most common and useful methods for, the synthesis of non-alpha-amino acids, particularly amino acids that are key synthetic intermediates or important compounds in their own right. Attention is paid to acyclic amino acids C3-C10 including amino alkanoic carboxylic acids, aminoalkenoic acids and aminoalkynoic acids.
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Editorial Reviews

Booknews
For scientists and advanced students in biological, medical, and pharmaceutical chemistry or physics, summarizes the main approaches to synthesizing amino acids in which the amino group is attached not to the carbon immediately adjacent to the carboxyl group (the alpha position), but to a carbon somewhere else in the chain. Describing techniques developed since 1962, focuses on the acyclic animo acids that have between three and ten carbons, especially aminoalkanoic carboxylic, animoalkenoic, and aminoalkynoic acids. Considers both chiral and achiral acids, and emphasizes the enentioselectivity of each synthetic process. Double spaced. Annotation c. Book News, Inc., Portland, OR (booknews.com)
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Product Details

  • ISBN-13: 9780824796044
  • Publisher: CRC Press
  • Publication date: 5/28/1995
  • Pages: 344
  • Product dimensions: 6.25 (w) x 9.25 (h) x 1.50 (d)

Table of Contents

Preface
Abbreviations
Ch. 1 Functional Group Exchange Strategies 1
1.1 Functional Group Transformations that Generate Amines 1
1.2 Functionalization to Form Carboxyl Groups 30
1.3 Functionalization of Amino Acids 38
1.4 Specialized Methods 46
Ch. 2 Cyclic Precursors 63
2.1 From Ketones 63
2.2 From Lactones and Anhydrides 67
2.3 From Lactams and Imides 71
2.4 From [beta]-Lactams 78
2.5 From Heterocycles 83
2.6 Diels-Alder Strategies 92
Ch. 3 Conjugate Addition Reactions 98
3.1 Amine Nucleophiles 98
3.2 Carbon Nucleophiles 107
Ch. 4 Condensations 114
4.1 Knoevenagel and Doebner Condensations 114
4.2 Mukaiyama Type Condensations 118
4.3 Enolate Anion Reactions 120
4.4 Condensation Reactions Involving Organozinc Intermediates 134
4.5 Specialized Condensation Reactions 136
Ch. 5 Diastereoselective and Enantioselective Syntheses 141
5.1 Amino Acid Refunctionalization 141
5.2 Diastereoselective and Enantioselective Reactions 163
5.3 Catalytic Hydrogenation with Chiral, Nonracemic Catalysts 181
Ch. 6 Biologically Important Amino Acids 189
6.1 GABA-ergic Compounds 189
6.2 GABOB and Carnitine 194
6.3 Statine and Related Compounds 206
6.4 Syntheses of Natural Products and Important Non-Natural Products 223
Ch. 7 Aminocyclic and Heterocyclic Amino Acids 243
Amino Acid Index 295
Author Index 311
Subject Index 333
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