Thioorthoesters in the Activated Pictet-Spengler Cyclization. Synthesis of 1-Thiosubstituted Tetrahydroisoquinolines and Carbon-Carbon Bond Formation via Sulfonyl Iminium Ions Generated from N,S-Sulfonyl Acetals

CLAUDIO C. SILVEIRA; CARMEM R. BERNARDI; TEODORO S. KAUFMAN

TETRAHEDRON LETTERS

Elsevier

Lugar: Amsterdam; Año: 2003 vol. 44 p. 6137 - 6140

0040-4039

The elaboration of 1-alkylthio- and 1-arylthio-tetrahydroisoquinolines by means of the activated Pictet?Spengler reaction of N-sulfonyl-_-phenethylamines with thioorthoesters as electrophiles, and their use as sulfonyl iminium ion precursors for carbon_carbon bond formation, leading to 1-substituted tetrahydroisoquinoline derivatives, is reported.