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

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 r...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Sun Hee, Wei, Han-Xun, Gao, Joe J., Li, Guigen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2002
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146431/
http://dx.doi.org/10.3390/70100089
_version_ 1783356391638958080
author Kim, Sun Hee
Wei, Han-Xun
Gao, Joe J.
Li, Guigen
author_facet Kim, Sun Hee
Wei, Han-Xun
Gao, Joe J.
Li, Guigen
author_sort Kim, Sun Hee
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6146431
institution National Center for Biotechnology Information
language English
publishDate 2002
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61464312018-11-19 Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide† Kim, Sun Hee Wei, Han-Xun Gao, Joe J. Li, Guigen Molecules Article 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. MDPI 2002-01-30 /pmc/articles/PMC6146431/ http://dx.doi.org/10.3390/70100089 Text en © 2002 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Kim, Sun Hee
Wei, Han-Xun
Gao, Joe J.
Li, Guigen
Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title_full Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title_fullStr Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title_full_unstemmed Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title_short Three-Component Halo Aldol Condensation of Thioacrylates with Aldehydes Mediated by Titanium (IV) Halide†
title_sort three-component halo aldol condensation of thioacrylates with aldehydes mediated by titanium (iv) halide†
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146431/
http://dx.doi.org/10.3390/70100089
work_keys_str_mv AT kimsunhee threecomponenthaloaldolcondensationofthioacrylateswithaldehydesmediatedbytitaniumivhalide
AT weihanxun threecomponenthaloaldolcondensationofthioacrylateswithaldehydesmediatedbytitaniumivhalide
AT gaojoej threecomponenthaloaldolcondensationofthioacrylateswithaldehydesmediatedbytitaniumivhalide
AT liguigen threecomponenthaloaldolcondensationofthioacrylateswithaldehydesmediatedbytitaniumivhalide

Ejemplares similares