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Anionic cascade reactions. One-pot assemblyof (Z)-chloro-exo-methylenetetrahydrofurans fromβ-hydroxyketones

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Schevenels, Florian [UCL] Marko, Istvan [UCL]

The assembly of (Z)-chloro-exo-methylenetetrahydrofurans by an original and connective anionic cascade sequence is reported. Base-catalysed condensation of β-hydroxyketones with 1,1-dichloroethylene generates, in moderate to good yields, the corresponding (Z)-chloro-exo-methylenetetrahydrofurans. Acidic treatment of this motif leads to several unexpected dimers, possessing unique structural features.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "Beilstein journal of organic chemisrty" - Vol. 9, no.9, p. 1319-1325 (03/07/13)
Peer reviewed yes
issn 1860-5397
e-issn 1860-5397
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
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Bibliographic reference Schevenels, Florian ; Marko, Istvan. Anionic cascade reactions. One-pot assemblyof (Z)-chloro-exo-methylenetetrahydrofurans fromβ-hydroxyketones. In: Beilstein journal of organic chemisrty, Vol. 9, no.9, p. 1319-1325 (03/07/13)
Permanent URL http://hdl.handle.net/2078.1/131851