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Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes

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Villemin, Elise [UCL] Robeyns, Koen [UCL] Robiette, Raphaël [UCL] Herent, Marie-France [UCL] Marchand-Brynaert, Jacqueline [UCL]

A practical route is described for the preparation of 1-phosphono-3(4-di)- substituted-1,3-butadienes based on the Horner-Wadsworth-Emmons (HWE) reaction. Their reactivity in the Diels-Alder (DA) reaction with three selected dienophiles is studied and compared to diethyl 1-phosphono-1,3-butadiene. A particular attention is given to the P-deprotection of cycloadducts from dibenzyl phosphonodienes. New phosphonated bicycles and tricycles have been obtained using this HWE/DA reaction sequence. © 2012 Elsevier Ltd. All rights reserved

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès mixte
Publication date 2013
Language Anglais
Journal information "Tetrahedron" - Vol. 69, no. 3, p. 1138-1147 (2013)
Peer reviewed yes
Publisher Pergamon ((United Kingdom) Kidlington)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliations UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
UCL - SSS/LDRI - Louvain Drug Research Institute
Keywords 1-Phosphonodienes ; Benzyl deprotection ; Diels-Alder reaction ; Horner-Wadsworth- Emmons reaction ; Phosphonic acid
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Bibliographic reference Villemin, Elise ; Robeyns, Koen ; Robiette, Raphaël ; Herent, Marie-France ; Marchand-Brynaert, Jacqueline. Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes. In: Tetrahedron, Vol. 69, no. 3, p. 1138-1147 (2013)
Permanent URL http://hdl.handle.net/2078/123953