Synthesis of substituted tetrahydroisoquinolines and benzo[d]azepines fromphthalan or isochroman and N-silylaldimines

The 4,4'-di-tert-butylbiphenyl-catalyzed lithiation of phthalan (1a) and is ochroman (1b) in THF at 0 degreesC affords the corresponding functionalized benzyllithiums 2, which by reaction with N-silylaldimines yield, after aci d-bose work-up, the expected amino alcohols 3. Successive treatment of thes e amino alcohols with thionyl chloride and sodium hydroxide yields the corr esponding substituted benzofused six- and seven-membered nitrogen-containin g heterocycles 4.