Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

Siang En Syu, De Wei Wang, Pei Yi Chen, Yi Ting Hung, Yi Wun Jhang, Tzu Ting Kao, Yu Ting Lee, Wenwei Lin

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.

Original languageEnglish
Pages (from-to)5943-5946
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number45
DOIs
Publication statusPublished - 2010 Nov 10

Keywords

  • Aldehyde
  • Chemoselectivity
  • Michael addition
  • Morita-Baylis-Hillman
  • Multicomponent reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst'. Together they form a unique fingerprint.

  • Cite this