Anti "cis effect" selectivity in the reaction of singlet oxygen with trisubstituted alkenes

Article abstract of DOI:10.1016/0040-4039(95)00742-U

In the reaction of singlet oxygen with certain trisubstituted alkenes, a strong preference for regioselectivity favoring hydrogen abstraction on that side of the olefin with one substituent has been recognized. These results are rationalized in terms of non bonded interactions and the lack of oxygen interaction with two allylic hydrogens in the same side of the double bond.