Synthesis of enantiopure 1,4-dioxanes, morpholines and piperazines from the reaction of chiral 1,2-diols, amino alcohols and diamines with vinyl selenones

The reactions of easily available vinyl selenones with enantiopure 1,2-diols, N-protected-1,2-aminoalcohols and diamines gave differently substituted enantiopure 1,4-dioxanes, morpholines and piperazines, respectively, in good to excellent yields. The same procedure was extended to the synthesis of thiomorpholine, benzodiazepine, and benzoxazepine. These reactions proceeded in one pot, in the presence of base, through a simple and novel application of the Michael initiated ring closure (MIRC) reactions. The formed heterocycles are a framework which is observed in a large number of pharmaceutical compounds