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

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

doi:10.3390/70100089

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

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

7 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 language	English
Pages (from-to)	89-95
Number of pages	7
Journal	Molecules
Volume	7
Issue number	1
DOIs	https://doi.org/10.3390/70100089
State	Published - Jan 2002

Keywords

Aldol reaction
Halide
Thioester

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10.3390/70100089

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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.",

keywords = "Aldol reaction, Halide, Thioester",

author = "Kim, {Sun Hee} and Wei, {Han Xun} and Gao, {Joe J.} and Guigen Li",

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AU - Kim, Sun Hee

AU - Wei, Han Xun

AU - Gao, Joe J.

AU - Li, Guigen

PY - 2002/1

Y1 - 2002/1

N2 - 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.

AB - 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.

KW - Aldol reaction

KW - Halide

KW - Thioester

UR - http://www.scopus.com/inward/record.url?scp=0345681820&partnerID=8YFLogxK

U2 - 10.3390/70100089

DO - 10.3390/70100089

M3 - Article

AN - SCOPUS:0345681820

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EP - 95

JO - Molecules

JF - Molecules

IS - 1

ER -

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

Abstract

Keywords

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