Organocatalytic Strategies for the Construction of Optically Active Imidazoles, Oxazoles, and Thiazoles

This study demonstrates the first enantioselective synthesis of hydroxyalkyl‐ and aminoalkyl‐substituted imidazoles, oxazoles, and thiazoles. The approach developed utilizes a highly effective one‐pot reaction cascade that consists of either an organocatalytic epoxidation or aziridination of α,β‐unsaturated aldehydes coupled with a [3+2]‐annulation, in which amidines, ureas, or thioureas act as effective 1,3‐dinucleophilic species. The methodology described benefits from low catalyst loadings, commercially and readily available starting materials, and mild reaction conditions.