An organocatalytic hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence: divergent synthesis of multi-substituted 2,3-dihydrofurans and 2,3-dihydropyrroles from cyanohydrins

Abstract

The first example of divergent synthesis of functionalized 2,3-dihydrofuran and 2,3-dihydropyrrole derivatives via a Lewis base-catalysed hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence is reported. The operational simplicity of the method allows for greater efficiency in the synthesis of a wide range of functionalized 2,3-dihydrofurans and 2,3-dihydropyrroles from readily accessible allylic cyanohydrins and activated alkynes in good to excellent yields under optimal conditions.