5 Scopus citations

Abstract

The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.

Original languageEnglish
Pages (from-to)12964-12972
Number of pages9
JournalJournal of Organic Chemistry
Volume86
Issue number18
DOIs
StatePublished - 17 Sep 2021

Scopus subject areas

  • Organic Chemistry

Keywords

  • 2H-AZIRINES
  • ACCESS
  • ALKYNES
  • ANTHRANILS
  • CARBENES
  • COUNTER ANIONS
  • EFFICIENT
  • GENERATION
  • INDUSTRIAL PERSPECTIVE
  • YNAMIDES

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