Magnesium Halide-Catalyzed Anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones

David A. Evans, C. Wade Downey, Jared T. Shaw, Jason S. Tedrow

Research output: Contribution to journalArticle

139 Scopus citations

Abstract

matrix presented Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2-OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.

Original languageEnglish (US)
Pages (from-to)1127-1130
Number of pages4
JournalOrganic Letters
Volume4
Issue number7
DOIs
StatePublished - Apr 4 2002
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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