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

Ming Zhang, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)12450-12455
Number of pages6
JournalChemistry - A European Journal
Volume23
Issue number51
DOIs
Publication statusPublished - 2017 Sep 12
Externally publishedYes

Keywords

  • asymmetric catalysis
  • bishydroxamic acid
  • cycloaddition reactions
  • indium
  • isoxazolidine

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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