A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines

Alexey Kuznetsov, Anton V. Gulevich, Donald J. Wink, Vladimir Gevorgyan

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.

Original languageEnglish (US)
Pages (from-to)9021-9025
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number34
DOIs
StatePublished - Aug 18 2014
Externally publishedYes

Keywords

  • aminoalkylation
  • diastereoselectivity
  • diazo compounds
  • heterocycles
  • triazolines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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