An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate

In Su Kim; Yun Jung Ji; Young Hoon Jung

doi:10.1016/j.tetlet.2006.08.040

An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate

In Su Kim
, Yun Jung Ji
, Young Hoon Jung

Department of Pharmacy

Sungkyunkwan University

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

An efficient stereoselective syntheses of (2S,3S)-3-hydroxypipecolic acid and (2R,3S)-2-hydroxymethylpiperidin-3-ol were achieved from p-anisaldehyde via the regioselective and diastereoselective introduction of an N-protected amine group using chlorosulfonyl isocyanate, ring-closing methathesis, and oxidation of p-methoxyphenyl group as the key steps.

Original language	English
Pages (from-to)	7289-7293
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2006.08.040
State	Published - 9 Oct 2006

Keywords

3-Hydroxypipecolic acid
Amination
Chlorosulfonyl isocyanate
Diastereoselectivity

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10.1016/j.tetlet.2006.08.040

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title = "An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate",

abstract = "An efficient stereoselective syntheses of (2S,3S)-3-hydroxypipecolic acid and (2R,3S)-2-hydroxymethylpiperidin-3-ol were achieved from p-anisaldehyde via the regioselective and diastereoselective introduction of an N-protected amine group using chlorosulfonyl isocyanate, ring-closing methathesis, and oxidation of p-methoxyphenyl group as the key steps.",

keywords = "3-Hydroxypipecolic acid, Amination, Chlorosulfonyl isocyanate, Diastereoselectivity",

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T1 - An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate

AU - Kim, In Su

AU - Ji, Yun Jung

AU - Jung, Young Hoon

PY - 2006/10/9

Y1 - 2006/10/9

N2 - An efficient stereoselective syntheses of (2S,3S)-3-hydroxypipecolic acid and (2R,3S)-2-hydroxymethylpiperidin-3-ol were achieved from p-anisaldehyde via the regioselective and diastereoselective introduction of an N-protected amine group using chlorosulfonyl isocyanate, ring-closing methathesis, and oxidation of p-methoxyphenyl group as the key steps.

AB - An efficient stereoselective syntheses of (2S,3S)-3-hydroxypipecolic acid and (2R,3S)-2-hydroxymethylpiperidin-3-ol were achieved from p-anisaldehyde via the regioselective and diastereoselective introduction of an N-protected amine group using chlorosulfonyl isocyanate, ring-closing methathesis, and oxidation of p-methoxyphenyl group as the key steps.

KW - 3-Hydroxypipecolic acid

KW - Amination

KW - Chlorosulfonyl isocyanate

KW - Diastereoselectivity

UR - https://www.scopus.com/pages/publications/33748296374

U2 - 10.1016/j.tetlet.2006.08.040

DO - 10.1016/j.tetlet.2006.08.040

M3 - Article

AN - SCOPUS:33748296374

SN - 0040-4039

VL - 47

SP - 7289

EP - 7293

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate

Abstract

Keywords

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