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Synlett 2009(5): 704-715  
DOI: 10.1055/s-0028-1087929
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

New Generation of Modular Nucleophilic Glycine Equivalents for the General Synthesis of α-Amino Acids

Vadim A. Soloshonok*, Hisanori Ueki, Trevor K. Ellis
Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
Fax: +1(405)3256111; e-Mail: vadim@ou.edu;
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Publikationsverlauf

Received 8 August 2008
Publikationsdatum:
24. Februar 2009 (online)

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Abstract

A review of the advances in the synthesis of sterically constrained α-amino acids, specifically the preparation of optically active β-substituted pyroglutamic acids via the homologation of a new generation of modular nickel(II)-complexed glycine equivalents, is herein presented. Following a brief overview of the general methods for the preparation of α-amino acids, paying close attention to the homologation of achiral glycine equivalents, the majority of this review is dedicated to the accomplishments of a new generation of modularly designed nucleophilic glycine equivalents. As one will see from this review, the key advantage of this new series of glycine equivalents is that the physical and chemical properties of these compounds can be altered to fit the requirements of the homologation technique desired. This modular approach has already been exploited to fine-tune the nickel(II)-complexed glycine equivalent for the asymmetric synthesis of a variety of β-substituted pyroglutamic acids via its Michael addition reaction with various (S)-3-(E)-enoyl-4-phenyloxazolidin-2-ones.

1 Introduction

2 Literature Examples of Achiral Glycine Equivalents

3 Picolinic Acid-Schiff Base Derived Achiral Glycine Equivalents

4 Modular Design of Achiral Nucleophilic Glycine Equivalents

5 Rational Control of Physicochemical Properties and Reactivity in a Series of Modular Nucleophilic Glycine Equivalents

6 Application of Modular Nucleophilic Glycine Equivalents for the General Asymmetric Synthesis of β-Substituted Pyroglutamic Acids

7 Disassembly of the Michael Addition Products, Isolation of the Target α-Amino Acids, and Recycling of the Starting Compounds

8 Elaboration of β-Substituted Pyroglutamic Acids into Various Sterically Constrained C5- and C6-α-Amino Acids

9 Summary

Key words

glycine equivalents - α-amino acids - sterically constrained chimeras - asymmetric synthesis - Michael additions

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43

Available from the Tokyo Chemical Industry, e.g. catalogue numbers P1738, P1737, and D3543.