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

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

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 r...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2002-01, Vol.7 (1), p.89-95
Hauptverfasser: Kim, Sun Hee, Wei, Han-Xun, Gao, Joe J., Li, Guigen
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Aldol reaction
halide
Organic chemistry
thioester
Titanium
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Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/70100089