α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones

Ming Zhang, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

13 被引用数 (Scopus)

抄録

1,3-Dipolar cycloaddition is a commonly exploited method to access 5-membered chemical entities with a variety of peripheral functionalities and their stereochemical arrangements. Nitrones are isolable 1,3-dipoles that exhibit sufficient reactivity toward electron-deficient olefins in the presence of Lewis acids to deliver highly substituted isoxazolidines. Herein we document that α,β-unsaturated amides, generally regarded as barely reactive in a 1,3-dipolar reaction manifold, were effectively activated using the designed 7-azaindoline auxiliary in an In(OTf)3/bishydroxamic acid catalytic system. The broad substrate scope and clean removal of the 7-azaindoline auxiliary from the product highlight the synthetic utility of the present catalysis.

本文言語English
ページ(範囲)12450-12455
ページ数6
ジャーナルChemistry - A European Journal
23
51
DOI
出版ステータスPublished - 2017 9 12
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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