Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide

Abstract

a,b-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.

Keywords

• Aldol reaction
• halide
• thioester