Enantioselective Construction of Cyclopropane Rings via Asymmetric Simmons-Smith Reaction of Allylic Alcohols

Article abstract of DOI:10.1246/cl.1992.61

The Simmons-Smith reaction starting from allylic alcohols using (R,R)-diethyl tartrate as a chiral auxiliary was found to proceed enantioselectively; i.e., the treatment of allylic alcohols with diethylzinc and diethyl tartrate, followed by the reaction with diethylzinc and diiodomethane, afforded the corresponding cyclopropylmethyl alcohols in optically active form.