Chiral amine thiourea-promoted enantioselective domino Michael-aldol reactions between 2-mercaptobenzaldehydes and maleimides

Liansuo Zu, Hexin Xie, Hao Li, Jian Wang, Wei Jiang, Wei Wang

Research output: Contribution to journalArticlepeer-review

108 Scopus citations

Abstract

An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenz-aldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single operation.

Original languageEnglish (US)
Pages (from-to)1882-1886
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number11-12
DOIs
StatePublished - Aug 2007
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Asymmetric synthesis
  • Michael addition
  • Organic catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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