STEREOCONTROLLED SYNTHESIS OF N-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES VIA CHROMIUM TRICARBONYL METHODOLOGIES

被引:18
作者
DAVIES, SG
机构
[1] The Dyson Perrins Laboratory, Oxford, OX1 3QY, South Parks Road
关键词
D O I
10.1016/0022-328X(90)83014-B
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two chromium tricarbonyl based methods are described for the stereocontrolled synthesis of N-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. Sequential deprotonation-alkylation reactions introduce substituents completely stereoselectively onto the 1- and 4-positions of N-methyl tetrahydroisoquinolines. Acid promoted cyclisations of (N-3,4-dimethoxybenzyl)N-methyl-2-amino-1-aryl ethanol chromium tricarbonyl complexes produce, stereospecifically with retention of configuration, the corresponding 4-phenyl-N-methyl tetrahydroisoquinolines. These cyclisations stereochemically complement those observed for the uncomplexed series. In all cases oxidative decomplexation efficiently releases the free elaborated N-methyl tetrahydroisoquinoline derivatives.
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页码:223 / 234
页数:12
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