DOI

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

    Research areas

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

ID: 87337614