Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation.

ABSTRACT: A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp³-sp² coupling reaction involving a 3-substituted 4-bromo-N-Boc-piperidine (Boc = tert-butoxycarbonyl) substrate as a key step. A 9:1 diastereoselectivity was obtained, while a control experiment involving a conformationally locked 3-substituted 4-bromo-tert-butyl cyclohexane ring proceeded with essentially complete stereoselectivity.

SUBMITTER: Despiau CF 

PROVIDER: S-EPMC4255755 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature