Synthesis of Substituted Tetrahydroisoquinolines and Benzo[d]azepines from Phthalan or Isochroman and N‐silylaldimines

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