Direct catalytic asymmetric intramolecular conjugate addition of thioamide to α,β-unsaturated esters

Yuta Suzuki, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Proton transfer allows efficient access to optically active five- and six-membered ring systems bearing ester and thioamide functionalities in an anti fashion; these ring systems are amenable to differential functional group manipulation. Direct catalytic, asymmetric, intramolecular conjugate addition of thioamide to α,β-unsaturated esters is described. In situ generated Cu thioamide enolate, by catalytic deprotonation, underwent the conjugate addition/protonation, to achieve the complete transformation (see scheme).

Original languageEnglish
Pages (from-to)11998-12001
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number43
DOIs
Publication statusPublished - 2011 Oct 17
Externally publishedYes

Keywords

  • atom economy
  • conjugate addition
  • cooperative catalysis
  • proton transfer
  • thioamides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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