Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine

Yeong Jiunn Jang, Siang En Syu, Yi Wun Jhang, Yu Ting Lee, Chia Jui Lee, Ko Wei Chen, Utpal Das, Wenwei Lin

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.

Original languageEnglish
Pages (from-to)2529-2541
Number of pages13
JournalMolecules
Volume17
Issue number3
DOIs
Publication statusPublished - 2012 Mar

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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