Stereoselective synthesis of 2,3-dihydropyrroles from terminal alkynes, azides, and α,β-unsaturated aldehydes via N-sulfonyl-1,2,3-triazoles

Tomoya Miura, Takamasa Tanaka, Kentaro Hiraga, Scott G. Stewart, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

135 Citations (Scopus)

Abstract

A stereoselective method for synthesis of trans-2,3-disubstituted 2,3-dihydropyrroles is reported. N-Sulfonyl-1,2,3-triazoles prepared from terminal alkynes generate α-imino rhodium carbene complexes, which when combined with α,β-unsaturated aldehydes produce trans-2,3- disubstituted dihydropyrroles. The method can be successfully applied to a one-pot process starting from terminal alkynes.

Original languageEnglish
Pages (from-to)13652-13655
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number37
DOIs
Publication statusPublished - Sep 18 2013
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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