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

被引:59
作者
NERINCKX, W
VANDEWALLE, M
机构
[1] State University of Gent, Department of Organic Chemistry, Laboratory for Organic Synthesis, B-9000 GENT, Krijgslaan, 281 (S
关键词
D O I
10.1016/S0957-4166(00)86331-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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.
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页码:265 / 276
页数:12
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