Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives

C. H. Lin; K. S. Yang; J. F. Pan; K. Chen

doi:10.1016/S0040-4039(00)01157-6

Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives

C. H. Lin, K. S. Yang, J. F. Pan, K. Chen

Department of Chemistry

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

33 Citations (Scopus)

Abstract

Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6815-6819
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)01157-6
Publication status	Published - 2000 Aug 26

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.",

author = "Lin, {C. H.} and Yang, {K. S.} and Pan, {J. F.} and K. Chen",

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T1 - Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls

T2 - Synthesis of β-mercaptocarboxylic acid derivatives

AU - Lin, C. H.

AU - Yang, K. S.

AU - Pan, J. F.

AU - Chen, K.

PY - 2000/8/26

Y1 - 2000/8/26

N2 - Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

AB - Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

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