Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides

Lucas L. Baldassari, Aurélien de la Torre, Jing Li, Diogo S. Lüdtke, Nuno Maulide

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

A novel ynamide preactivation strategy enables the use of otherwise incompatible reagents and allows preparation of α,β-disubstituted enamides with high regio- and stereoselectivity. Mechanistic analysis reveals the intermediacy of a triflate-bound intermediate as a solution-stable, effective keteniminium reservoir, whilst still allowing subsequent addition of organometallic reagents.

Original languageEnglish
Pages (from-to)15723-15727
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number49
DOIs
Publication statusPublished - 2017 Dec 4

Keywords

  • keteniminium
  • preactivation
  • regioselectivity
  • stereoselectivity
  • ynamides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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