The Use of Lewis Acids for Repairing Chemoselectivity of the Organocatalyzed Morita-Baylis-Hillman Reaction

Amit Fallek, Moshe Portnoy*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A substantial improvement in the chemoselectivity of the Morita-Baylis-Hillman reaction was realized by adding a diimino- or diaminopyridine coordination site within the backbone of bis-imidazole organocatalysts and using Lewis acids situated at this coordination site. The optimal outcome of 90–95% selectivity was achieved by proper matching of the catalyst/additive pair, as well as their respective amount (0.4 equiv. of AgOAc per 1 equiv. of diaminopyridine-incorporating catalyst).

Original languageEnglish
Pages (from-to)3175-3179
Number of pages5
JournalChemistrySelect
Volume4
Issue number11
DOIs
StatePublished - 22 Mar 2019

Keywords

  • Baylis-Hillman reaction
  • Lewis acids
  • chemoselectivity
  • cooperative catalysis
  • organocatalysis
  • synthetic methods

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