Direct catalytic asymmetric vinylogous conjugate addition of unsaturated butyrolactones to α,β-unsaturated thioamides

Liang Yin, Hisashi Takada, Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α,β- and β,γ-unsaturated butyrolactones to α,β-unsaturated thioamides with perfect atom economy. When using α-angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol % catalyst loading was sufficient to complete the reaction necessary to construct consecutive tri- and tetrasubstituted stereogenic centers in a highly diastereo- and enantioselective fashion. Soft spot: Soft Lewis acid/Brønsted base cooperative catalysts have enabled the title reaction of α,β- and β,γ- unsaturated butyrolactones with perfect atom economy. When using α-angelica lactone and its derivatives as pronucleophiles, a 0.5 mol % catalyst loading was sufficient to complete the reaction to construct consecutive tri- and tetrasubstituted stereogenic centers in a highly diastereo- and enantioselective fashion.

Original languageEnglish
Pages (from-to)5327-5331
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number21
DOIs
Publication statusPublished - 2014 May 19
Externally publishedYes

Keywords

  • asymmetric catalysis
  • copper
  • heterocycles
  • Michael addition
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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