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Molecules 2002, 7(1), 89-95; doi:10.3390/70100089

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

, ,  and *
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock TX 79409-1061, USA
* Author to whom correspondence should be addressed.
Received: 28 June 2001 / Revised: 19 December 2001 / Accepted: 21 December 2001 / Published: 30 January 2002
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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 Aldol reaction; halide; thioester
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Kim, S.H.; Wei, H.-X.; Gao, J.J.; Li, G. Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide. Molecules 2002, 7, 89-95.

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