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Communication | Regular issue | Vol 32, No. 12, 1991, pp.2311-2314
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5879
Diastereoselective Synthesis of 2,6-Disubstituted 3-Hydroxy Piperidine Derivatives by an Application of Radical Cyclization

Yoko Yuasa, Shinzo Kano, and Shiroshi Shibuya*

*Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

N-[α-(2-Bromo-1-butenyl)-α-methyl]oxazolin-2-one (7) and N-[α-(2-bromo-1-butenyl)-α-pyranyloxyethyl]oxazolin-2-one (14), obtained by starting with ethyl acetoacetate, were treated with tributyltin hydride in the presence of AIBN afforded the cyclization products (8) and (15), respectively, with high diastereoselectivity. Conversion of the 8-methyleneoxazolidinopiperidine (15) to the 6-hydroxyethyl-2-hydroxymethyl-3-hydroxypiperidine derivative (18) was described.