Diastereoselective synthesis of (1S,2S,3R,6S) 3-chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

Article abstract of DOI:10.1016/0040-4020(96)00167-6

While attempting to synthesize a potential inhibitor of the biosynthesis step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity.