A mild and efficient method for the synthesis of a new optically active diallyl selenide and its catalytic activity in the allylic chlorination of natural terpenes

A mild and convenient method for the synthesis of a new optically active bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide 1 from the corresponding bicyclic terpene is described. The structure of the obtained organoselenium compound was established using H-1, C-13, Se-77-NMR spectroscopy and X-ray diffraction studies. Its application as a catalyst in the allylic chlorination of terpenic olefins has been successfully investigated under mild conditions. The reaction showed high selectivity affording the corresponding chlorides in good to excellent yields. The use of enantiomerically pure monoterpenes as starting materials allowed the preparation of asymmetric allyl chlorides through a process controlled by the substrate.