ASYMMETRIC ALKYLATION OF ALPHA-ARYL SUBSTITUTED CARBONYL-COMPOUNDS BY MEANS OF CHIRAL PHASE-TRANSFER CATALYSTS - APPLICATIONS FOR THE SYNTHESIS OF (+)-PODOCARP-8(14)-EN-13-ONE AND OF (-)-WY-16,225, A POTENT ANALGESIC AGENT

Asymmetric induction in the alkylation (alkyl halides and enones) of α-aryl substituted ketones, esters and lactones by means of CPTC has been evaluated. The catalysts used are the bromides of N-(p-trifluoromethyl) benzyl derivatives of cinchonine, cinchonidine, dihydrocinchonine and dihydrocinchonidine. The potential of the method is illustrated by the asymmetric synthesis of (+)-podocarp-8(14)-ene-13-one (13) and of (-)-Wy-16,225 (10), a bridged aminotetralin with potent analgesic properties. © 1990.