title: 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-sp2coupling 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.
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK http://www.southampton.ac.uk/chemistry/about/staff/linclau.page.
authors.forename: Carole F
authors.initials: CF
authors.lastname: Despiau
authors.affiliation: GlaxoSmithKline, Medicines Research Centre Gunnels Wood Road, Stevenage SG1 2NY, UK.
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Dominey
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK http://www.southampton.ac.uk/chemistry/about/staff/linclau.page.
authors.forename: David C
authors.initials: DC
authors.lastname: Harrowven
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK http://www.southampton.ac.uk/chemistry/about/staff/linclau.page.
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
keywords: Cobalt; Cross-coupling; Homogeneous catalysis; Nitrogen heterocycles; Radicals; Total synthesis