Near Absolute Regio-, Diastereo-, and Enantioselectivity in a Palladium Catalyzed Alkylation Using an Uncommon Chiral Auxiliary

Article abstract of DOI:10.1002/recl.19921110107

Condensation of R-(+)-1-(2-chlorophenyl)-2,2-dimethyl-propan-1,3-diol (2) with a derivative (1) of 1-formylcyclohexene substituted in the 3-position with an acetoxy group proceeded with absolute stereospecificity at the acetal center.Catalytic alkylation of the ?-allyl complex obtained upon reaction with Pd with the anion of dimethylmalonate proceeded at the 3-position of the cyclohexyl ring with complete stereocontrol.