Synthesis of new chiral N-heterocyclic diselenides and their application in the alkoxyselenylation reaction

This paper describes the synthesis of chiral diselenides based on 2-azabicycloalkane or the pyrrolidine skeleton using in situ generated Na 2 Se 2 as an efficient selenylating reagent. All the diselenides were obtained in moderate yields under mild conditions. The well-defined enantio- and diastereomerically pure compounds were tested in the asymmetric alkoxyselenylation of alkenes yielding products with diastereoisomeric excess up to >99%. Novel chiral diselenides based on a cyclic or bicyclic backbone were applied in the highly diastereoselective methoxyselenylation of styrene.