Lewis Acid Promoted Trapping of Chiral Aza-enolates

Francesco Lanza, Juana M. Pérez Galera, Ravindra P. Jumde, Syuzanna R. Harutyunyan*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)
101 Downloads (Pure)

Abstract

We present a study on sequential conjugate addition of Grignard reagents to alkenyl-heteroarenes followed by trapping of the resulting enolates, yielding moderate to good diastereoselectivities. Contrary to conventional wisdom, one-pot conjugate addition/trapping using two reactive Michael acceptors in combination with Grignard reagents can proceed via conjugate addition to the least reactive Michael acceptor. This unusual chemoselectivity is triggered by the presence of a Lewis acid, reverting the usual reactivity order of Michael acceptors.

Original languageEnglish
Pages (from-to)1253-1262
Number of pages10
JournalSynthesis
Volume51
Issue number5
DOIs
Publication statusPublished - Mar-2019

Keywords

  • aza-enolate trapping
  • copper catalyst
  • Lewis acid
  • conjugate addition
  • one-pot reaction
  • TANDEM CONJUGATE ADDITION
  • GRIGNARD-REAGENTS
  • ASYMMETRIC-SYNTHESIS
  • CATALYZED ADDITION
  • ALDOL REACTIONS
  • ALKYLATION
  • KETONES
  • EFFICIENT
  • LIGAND
  • ESTERS

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