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

doi:10.1016/S0040-4039(01)01223-0

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 journal › Article › peer-review

54 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 language	English (US)
Pages (from-to)	6223-6225
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(01)01223-0
State	Published - Sep 3 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01223-0

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

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.",

author = "Jaemoon Lee and Thoa Hoang and Stephanie Lewis and Weissman, \{Steven A.\} and David Askin and Volante, \{R. P.\} and Reider, \{P. J.\}",

year = "2001",

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doi = "10.1016/S0040-4039(01)01223-0",

language = "English (US)",

volume = "42",

pages = "6223--6225",

journal = "Tetrahedron Letters",

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T1 - Asymmetric synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine via ring expansion

AU - Lee, Jaemoon

AU - Hoang, Thoa

AU - Lewis, Stephanie

AU - Weissman, Steven A.

AU - Askin, David

AU - Volante, R. P.

AU - Reider, P. J.

PY - 2001/9/3

Y1 - 2001/9/3

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0035801823

UR - https://www.scopus.com/pages/publications/0035801823#tab=citedBy

U2 - 10.1016/S0040-4039(01)01223-0

DO - 10.1016/S0040-4039(01)01223-0

M3 - Article

AN - SCOPUS:0035801823

SN - 0040-4039

VL - 42

SP - 6223

EP - 6225

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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