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

Jaemoon Lee, Thoa Hoang, Stephanie Lewis, Steven A. Weissman, David Askin, R. P. Volante, P. J. Reider

Research output: Contribution to journalArticle

51 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6223-6225
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number36
DOIs
StatePublished - Sep 3 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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