Abstract
The trimethylsilyl group has been shown to be effective as an activating group for ipso attack in the Pictet-Spengler reaction to control the regiochemistry in tetrahydroisoquinoline synthesis. In this manner, 2-(2-trimethylsilyl-3-methoxyphenyl)ethylamine was cyclized and N-methylated to give regiospecifically 8-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline while the non-silylated compound gave only the 6-methoxy isomer.
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