Enantiopure synthesis of side chain-modified α-amino acids and 5-cis-alkylprolines

Amar R. Mohite, Ramakrishna G. Bhat

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A short, concise synthesis of enantiopure, side chain-modified α-amino acids such as 4-oxo-l-norvaline, 6-oxo-l-homonorleucine, and 5-cis-alkyl prolines is described. Knoevenagel condensation of l-aminocarboxylate-derived β-ketoesters with aldehydes followed by reductive decarboxylation results in unnatural α-amino acids in good yield. A fluorescent amino acid is synthesized using a similar protocol. These studies show that aminocarboxylate-derived β-ketoesters are very useful intermediates and the method employed is both general and practical for the preparation of γ(δ)-oxo α-amino acids and alkylprolines.

Original languageEnglish
Pages (from-to)5423-5428
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number12
DOIs
StatePublished - 15 Jun 2012
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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