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

摘要

While attempting to synthesize a potential inhibitor of the biosynthetic step of formation of PEG, 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 diastereoselcctivity. [References: 24]