Synthesis and reactions of the optically active selenols derived from monoterpenes Dedicated to Professor Jacek Gawronski on the occasion of his 70th birthday

Article abstract of DOI:10.1016/j.tetasy.2013.07.018

A convenient methodology for the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic rearrangement of the in situ generated allylic selenoxides.