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Paper | Regular issue | Vol 60, No. 6, 2003, pp.1377-1385
Published online, 21st April, 2003
DOI: 10.3987/COM-03-9750
Novel Synthesis of 5-Oxomorpholine Derivative by Cyclization of Δ1-Dehydrodipeptide

Dai Yoshioka, Keiji Inoue, Yasuchika Yonezawa, and Chung-gi Shin*

*Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

A convenient synthesis of novel 6-disubstituted 5-oxomorpholine-3- carboxylate derivatives (5) by stereoselective cyclization of Δ1-dehydrodipeptides, Boc-ΔVal-L-AA-OMe (AA=Ser, Thr, HyVal) with t-BuOCl or N-halosuccinimide is described. Furthermore, the configuration of 5 was determined by single crystal X-Ray analysis.