Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles

Mikhail Zibinsky, Valery V. Fokin

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.

Original languageEnglish
Pages (from-to)4870-4872
Number of pages3
JournalOrganic Letters
Volume13
Issue number18
DOIs
Publication statusPublished - 16 Sep 2011
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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