New chiral selenium electrophiles derived from functionalized terpenes

A convenient method for the synthesis of optically active dialkyl diselenides derived from bicyclic terpenes functionalized with hydroxy, etheral, sulfide, and selenide groups is described. The diselenides were used for a synthesis of chiral electrophilic selenium reagents, then in the asymmetric selenenylation of styrene and selenocyclization with o-allylphenol. The influence of nonbonding selenium-heteroatom interactions in the generated organoselenium electrophiles on the stereoselectivity of an addition reaction has been investigated. Calculations by a DFT method on a B3LYP (6–311G (d)) level, confirmed the existence of nonbonded selenium–heteroatom interactions in the investigated systems.