Thiourea-amine catalysed asymmetric synthesis of functionalised epoxides

Bi-or multifunctional thiourea-amines are highly popular organocatalysts used for the C-C, C-N, and C-S bonds formation and in cascade reactions to prepare several heterocyclic compounds. More recently, thiourea-amines displayed useful catalytic activity to prepare functionalised epoxides via asymmetric epoxidation of electron-poor alkenes and kinetic resolution of racemic epoxides. In this personal account we present the results achieved by using this class of organocatalysts, which enabled the synthesis of a variety of functionalised epoxides in good to high yield, diastereo- and enantioselectivity. The optically active epoxides proved to be useful synthetic intermediates for further derivatization to heterocyclic or acyclic derivatives, bearing tertiary and quaternary stereocenters.