Asymmetric synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine via ring expansion
2001; Elsevier BV; Volume: 42; Issue: 36 Linguagem: Inglês
10.1016/s0040-4039(01)01223-0
ISSN1873-3581
AutoresJaemoon Lee, Thoa Hoang, Stephanie Lewis, Steven A. Weissman, David Askin, R. P. Volante, Paul J. Reider,
Tópico(s)Chemical Synthesis and Analysis
ResumoA 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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