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

✍ Scribed by Claudio C Silveira; Carmem R Bernardi; Antonio L Braga; Teodoro S Kaufman

• Book ID: 104254076
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 119 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01452-7

✦ Synopsis

The elaboration of 1-alkylthio-and 1-arylthio-tetrahydroisoquinolines by means of the activated Pictet-Spengler reaction of N-sulfonyl-b-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.