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

Schevenels, Florian;Marko, Istvan
(2013) Beilstein Journal of Organic Chemistry — Vol. 9, n° 9, p. 1319-1325 (03/07/13) (2013)

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Authors
  • Schevenels, FlorianUCLouvain
    Author
  • Marko, IstvanUCLouvain
    Author
Abstract
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.
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Schevenels, F., & Marko, I. (2013). Anionic cascade reactions. One-pot assemblyof (Z)-chloro-exo-methylenetetrahydrofurans fromβ-hydroxyketones. Beilstein Journal of Organic Chemistry, 9(9), 1319-1325 (03/07/13). https://doi.org/10.3762/bjoc.9.148 (Original work published 2013)