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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)6815-6819
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number35
DOIs
Publication statusPublished - 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

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 journalArticle

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