Asymmetric Synthesis of Quaternary α-Amino Acids and Their Phosphonate Analogues

Asymmetric synthesis of α‐amino acids and their phosphonate analogues has received considerable attention due to their diverse biological activities. Quaternary α‐amino acids and their phosphonate analogues are often more resistant to chemical and enzymatic degradation and therefore have been target...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2014-12, Vol.3 (12), p.1234-1260
Main Authors: Bera, Kalisankar, Namboothiri, Irishi N. N.
Format: Article
Language:English
Subjects:
asymmetric synthesis
Mannich reaction
quaternary stereocenters
α-amino acids
α-aminophosphonates
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Summary:Asymmetric synthesis of α‐amino acids and their phosphonate analogues has received considerable attention due to their diverse biological activities. Quaternary α‐amino acids and their phosphonate analogues are often more resistant to chemical and enzymatic degradation and therefore have been targets of various synthetic endeavors. This Focus Review provides a summary of recent approaches to catalytic asymmetric synthesis of quaternary α‐amino acids and α‐aminophosphonates. Building the building blocks: This review focuses on various recent approaches to the asymmetric synthesis of quaternary α‐amino acids and their transition‐state analogues, and quaternary α‐aminophosphonic acids. The enantio‐ and diastereoselectivities of these approaches are emphasized, as are the syntheses of intermediates in the preparation of natural products and other bioactive compounds. Pg=protecting group.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402178