The first enantioselective halo aldol reaction of ethyl propiolate and aldehydes

Dianjun Chen, Cody Timmons, Junying Liu, Allan Headley, Guigen Li

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29 Scopus citations

Abstract

The first enantioselective halo aldol reaction of ethyl propiolate with aldehydes has been established by using Jacobsen's chiral cyclohexylsalen ligand. The reaction was conducted at -20 °C in dichloromethane with Et 2AlI as the source of halogen and Lewis acid promoter. Excellent geometric selectivity (only the Z isomer) has been achieved for all 14 examples examined. The reaction works well with aromatic aldehydes; it also works with aliphatic aldehydes and α,β-unsaturated aldehydes, albeit with diminished yields and ee. This method provides the first enantioselective synthesis of β-iodo Morita-Baylis-Hillman (MBH) esters.

Original languageEnglish
Pages (from-to)3330-3335
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
StatePublished - Jul 26 2004

Keywords

  • Aldol reactions
  • Chiral salen
  • Enantioselectivity
  • Morita-Baylis-Hillman esters

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