Asymmetric synthesis of (2S, 3S)-3-hydroxy-2-phenylpiperidine via ring expansion

J Lee, T Hoang, S Lewis, SA Weissman, D Askin…

Index: Lee, Jaemoon; Hoang, Thoa; Lewis, Stephanie; Weissman, Steven A; Askin, David; Volante; Reider Tetrahedron Letters, 2001 , vol. 42, # 36 p. 6223 - 6225

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Citation Number: 45

Abstract

A catalytic highly enantioselective (99% ee) preparation of N-tert-butyloxycarbonyl-(2S, 3S)- 3-hydroxy-2-phenyl-piperidine and N-tert-butyloxycarbonyl-(2S)-2-phenyl-piperidin-3-one was developed using an intramolecular epoxide opening followed by ring expansion. The cis-epoxide starting material was available in high ee via Jacobsen epoxidation.