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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)6815-6819
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number35
DOIs
Publication statusPublished - 2000 Aug 26

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this