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Paper | Regular issue | Vol 27, No. 6, 1988, pp.1437-1443
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4515
Diastereoselective Synthesis of Hexahydro-3H-oxazolo[3,4-a]pyridin-3-one Derivatives by Cyclization of α-Acylaminoradical-Olefin System

Shinzo Kano,* Yoko Yuasa, Kenji Asami, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The substituent effect in α-acylaminoradical-olefin cyclization was examined. Treatment of 4-phenylthiooxazolidin-2-ones (10a-f) with tri-n-buytltin hydride in the presence of AIBN yielded 6,7-cis-6,8a-trans-6-alkyl-7-arylhexahydrooxazolo[3,4-a]pyridin-3-ones (11a-f), respectively, with high diastereoselectivity.