Asymmetric alkylation of α-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

Article abstract of DOI:10.1016/S0957-4166(00)86331-4

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.