An asymmetric synthesis of 2-substituted piperidines through ozonolysis of cyclopentenes and reductive aminocyclization

…, N Sakai, M Hamada, Y Yamamoto, J Oda

Index: Kawaguchi, Mamoru; Hayashi, Osamu; Sakai, Noriyuki; Hamada, Masayuki; Yamamoto, Yukio; Oda, Jun'ichi Agricultural and Biological Chemistry, 1986 , vol. 50, # 12 p. 3107 - 3112

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Citation Number: 13

Abstract

By the action of ozone, sodium cyanoborohydride and the optically active benzylic amines 2, the 1-substituted cyclopentenes 1, 5 and 9 were converted to a diastereoisomeric mixture of 1, 2-disubstituted piperidines (3, 6 and 10), respectively. Hydrogenation of these compounds and the following work-up yielded optically active 2-alkylpiperidines (4, up to 68% ee.), pipecolic acid (7, 84% ee.) and 2-(hydroxymethyl) piperidine (11, up to 85% ee.). ...