Canadian Journal of Chemistry

The preparation of (S)-3, 4-dehydroproline from (2 S, 4 R)-4-hydroxyproline

H Rüeger, MH Benn

Index: Rueeger, Heinrich; Benn, M. H. Canadian Journal of Chemistry, 1982 , vol. 60, p. 2918 - 2920

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Citation Number: 34

Abstract

(2 S, 4 R)-N-Benzyloxycarbonyl-4-tosyloxyproline methyl ester, readily prepared from commercially available (2 S, 4 R)-N-benzyl-oxycarbonyl-4-hydroxyproline, was converted to (S)-3, 4-dehydroproline of high enantiomeric purity by a process which involved a highly regioselective phenylselenoxide elimination to introduce the olefinic function.