Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from D-allal- and D-galactal-derived vinyl epoxides

Abstract Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) ( C -nucleophiles) and benzyl carbamate ( N -nucleophile), D-allal- and D-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis - and trans -2,5-disubstituted-2,5-dihydrofurans.