Assembly of dimethyl acetylenedicarboxylate and phosphanes with aldehydes leading to γ-lactones bearing α-phosphorus ylides as wittig reagents

Jie Cheng Deng, Fu Wei Chan, Chih Wei Kuo, Chun An Cheng, Chien Yu Huang, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

We report herein a convenient route to the synthesis of aryl-substituted γ-lactones bearing an α-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl-or trialkylphosphanes in moderate to good yields. The formation of γ-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.

Original languageEnglish
Pages (from-to)5738-5747
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number29
DOIs
StatePublished - 1 Oct 2012

Keywords

  • Lactones
  • Multicomponent reactions
  • Phosphanes
  • Wittig reactions
  • Ylides

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