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

A total synthesis of paroxetine is reported, with a diastereo-selective and diastereoconvergent cobalt-catalysed sp(3)-sp(2) coupling reaction involving a 3-substituted 4-bromo-N-Bocpiperidine (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.