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

Author(s): Sun Hee Kim | Han-Xun Wei | Joe J. Gao | Guigen Li

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 1; Start page: 89; Date: 2002;
Original page

Keywords: Aldol reaction | halide | thioester

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.