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

✍ Scribed by Jaemoon Lee; Thoa Hoang; Stephanie Lewis; Steven A Weissman; David Askin; R.P Volante; P.J Reider

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
71 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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