Proline-catalyzed synthesis of α-substituted (E)-α,β-unsaturated aldehydes from epoxides

Abstract

A novel, simple and metal-free tandem approach for synthesizing α-substituted (E)-α,β-unsaturated aldehyde derivatives through acid-catalyzed epoxide rearrangement and organocatalyzed aldol condensation processes has been described. This transformation has a broad substrate scope under mild conditions, including epoxides and aldehydes containing diverse functional groups, resulting in moderate to high yields of the desired products. Eventually, large-scale reactions and the synthesis of some bioactive molecules are used to demonstrate the potential applicability of the developed method.