First asymmetric synthesis of chiral β-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions

Xin Xu, Dianjun Chen, Han Xun Wei, Guigen Li, Tom Ling Xiao, Daniel W. Armstrong

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A new asymmetric approach to chiral β-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and α,β-acetylenic menthyl ester in dichloromethane at -23°C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.

Original languageEnglish
Pages (from-to)139-142
Number of pages4
JournalChirality
Volume15
Issue number2
DOIs
StatePublished - 2003

Keywords

  • Asymmetric aldol reaction
  • Baylis-Hillman adducts
  • Conjugate addition
  • Diethylaluminum iodide
  • Menthol auxiliary

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