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

Ming Zhang, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

29 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5525-5529
ページ数5
ジャーナルChemistry - A European Journal
22
16
DOI
出版ステータスPublished - 2016 4 11
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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