Asymmetric Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones

B. Dikic, P.A. Gordon, S.G. Pyne, Brian Skelton, Allan White

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S-methylcysteine, and their highly exo-selective Diels-Alder reactions with cyclic dienes are described. (1R,2S,4S)-2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid has been prepared in 92% e.e. by these methods. A number of the products have been characterized by single-crystal X-ray methods, and their structure systematics examined.
Original languageEnglish
Pages (from-to)73-93
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume46
DOIs
Publication statusPublished - 1993

Fingerprint

Dive into the research topics of 'Asymmetric Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones'. Together they form a unique fingerprint.

Cite this