Three-component halo aldol condensation of thioacrylates with aldehydesmediated by titanium (IV) halide

Sun Hee Kim, Han Xun Wei, Joe J. Gao, Guigen Li

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

α,β-Ethyl thioacrylate was difuctionalized by a tandem X-C/C=C bond formation reaction. The new system uses Ti (IV) halide as both the Lewis acidic promoter and the halogen source for the Michael-type addition onto the thioacrylate. The titanium enolate species resulting from Michael-type addition react with aldehydes followed by dehydration to afford trisubstituted olefin products. Complete geometric selectivity (>95%) and up to 72% yield have been obtained for 7 examples.

Original languageEnglish
Pages (from-to)89-95
Number of pages7
JournalMolecules
Volume7
Issue number1
DOIs
StatePublished - Jan 2002

Keywords

  • Aldol reaction
  • Halide
  • Thioester

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