Stereoselective epoxidation of a 5,6,6-trisubstituted cyclohex-2-enone
Abstract
Alkaline hydroperoxidation of a cis/trans mixture of 5,6-dimethyl-6-allylcyclohex-2-enone (4 : 1) has led to a pair of epoxides (ratio 3 :1 ) derived only from the cis isomer, whose separation was achieved chromatographically and the relative stereochemistry defined by crystal structure analysis of an ozonolysis product.