Anionic cascade reactions. One-pot assembly of (Z)-chloro-exo-methylenetetrahydrofurans from β-hydroxyketones

IE Markó, FT Schevenels

Index: Marko, Istvan E.; Schevenels, Florian T. Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1319 - 1325

Full Text: HTML

Citation Number: 2

Abstract

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.