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Communication | Regular issue | Vol 26, No. 11, 1987, pp.2805-2809
Published online, 1st January, 1970
DOI: 10.3987/R-1987-11-2805
Diastereoselective Synthesis of 2,3-cis-Alkyl-3-oxygenated Piperidine Derivatives by Titanium Mediated Intramolecular Cyclization of α-Aminoacetal-allylsilane System

Shinzo Kano, Tsutomu Yokomatsu, Haruo Iwasawa, and Shiroshi Shibuya

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

Abstract

(2S,3S)-2-Alky1-3-oxygenated 5-methylenepiperidines were obtained with high diastereoselectivity by cyclization of N-methoxycarbonyl-N-silylmethallyl-α-alkylaminoacetaldehyde ethyleneacetals with TiCl3 (OPri).