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Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes

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Marko, Istvan [UCL] Murphy, F. Kumps, Lucien [UCL] Ates, Ali [UCL] Touillaux, Roland Dolan, S

High yields of di- and tri-substituted alkenes are: obtained by a modification of the Julia-Lythgoe olefination reaction involving the in situ capture of intermediate beta -alkoxy-sulfones by benzoyl or trimethylsilyl chloride, followed by SmI2-mediated reductive elimination. This novel protocol also provides a connective preparation of dienyl ethers, which are important partners in Diels-Alder cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2001
Language Anglais
Journal information "Tetrahedron" - Vol. 57, no. 13, p. 2609-2619 (2001)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords alkenes ; olefination ; sulfones ; Julia reaction ; samarium
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Bibliographic reference Marko, Istvan ; Murphy, F. ; Kumps, Lucien ; Ates, Ali ; Touillaux, Roland ; et. al. Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes. In: Tetrahedron, Vol. 57, no. 13, p. 2609-2619 (2001)
Permanent URL http://hdl.handle.net/2078.1/42834