Electrophilic Activation of α,β-Unsaturated Amides: Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated γ-Butyrolactones

Ming Zhang, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

Although catalytic asymmetric conjugate addition reactions have remarkably advanced over the last two decades, the application of less electrophilic α,β-unsaturated carboxylic acid derivatives in this useful reaction manifold remains challenging. Herein, we report that α,β-unsaturated 7-azaindoline amides act as reactive electrophiles to participate in catalytic diastereo- and enantioselective vinylogous conjugate addition of γ-butyrolactones in the presence of a cooperative catalyst comprising of a soft Lewis acid and a Brønsted base. Reactions mostly reached completion with as little as 1 mol % of catalyst loading to give the desired conjugate adducts in a highly stereoselective manner.

Original languageEnglish
Pages (from-to)5525-5529
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number16
DOIs
Publication statusPublished - 2016 Apr 11
Externally publishedYes

Keywords

  • asymmetric catalysis
  • azaindoline
  • butenolide
  • conjugate addition
  • cooperative catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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