Stereocontrolled approach to phenyl cyclitols from (SR)-[(p-tolylsulfinyl)methyl]-p-quinol.

Reactions of enantiopure (SR)-[(p-tolylsulfinyl)methyl]-p-quinol with ArAlMe(2) reagents allowed a highly diastereoselective 1,4-addition of the aryl group with an efficient desymmetrization of the prochiral cyclohexadienone moiety. The asymmetric synthesis of phenyl-substituted polyoxygenated cyclohexane derivatives was achieved by combining this reaction with a stereoselective reduction and elimination of the beta-hydroxysulfoxide, after oxidation to sulfone, to recover a carbonyl group, and a stereoselective epoxidation.