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; Kwunmin 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, Kwunmin Chen

Department of Chemistry

Research output: Contribution to journal › Article

32 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

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Camphor

Stereoselectivity

Lewis Acids

Carboxylic Acids

Sulfhydryl Compounds

Derivatives

Acids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Lin, C. H., Yang, K. S., Pan, J. F., & Chen, K. (2000). Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives. Tetrahedron Letters, 41(35), 6815-6819. https://doi.org/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. / Lin, C. H.; Yang, K. S.; Pan, J. F.; Chen, Kwunmin.

In: Tetrahedron Letters, Vol. 41, No. 35, 26.08.2000, p. 6815-6819.

Research output: Contribution to journal › Article

Lin, CH, Yang, KS, Pan, JF & Chen, K 2000, 'Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives', Tetrahedron Letters, vol. 41, no. 35, pp. 6815-6819. https://doi.org/10.1016/S0040-4039(00)01157-6

Lin CH, Yang KS, Pan JF, Chen K. Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives. Tetrahedron Letters. 2000 Aug 26;41(35):6815-6819. https://doi.org/10.1016/S0040-4039(00)01157-6

Lin, C. H. ; Yang, K. S. ; Pan, J. F. ; Chen, Kwunmin. / Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls : Synthesis of β-mercaptocarboxylic acid derivatives. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 35. pp. 6815-6819.

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10.1016/S0040-4039(00)01157-6