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

A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp(3)–sp(2) 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 contr...

Descripción completa

Detalles Bibliográficos
Autores principales: Despiau, Carole F, Dominey, Andrew P, Harrowven, David C, Linclau, Bruno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4255755/
https://www.ncbi.nlm.nih.gov/pubmed/25505371
http://dx.doi.org/10.1002/ejoc.201402108
_version_ 1782347483399061504
author Despiau, Carole F
Dominey, Andrew P
Harrowven, David C
Linclau, Bruno
author_facet Despiau, Carole F
Dominey, Andrew P
Harrowven, David C
Linclau, Bruno
author_sort Despiau, Carole F
collection PubMed
description A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp(3)–sp(2) 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.
format Online
Article
Text
id pubmed-4255755
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher WILEY-VCH Verlag
record_format MEDLINE/PubMed
spelling pubmed-42557552014-12-08 Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation Despiau, Carole F Dominey, Andrew P Harrowven, David C Linclau, Bruno European J Org Chem Full Papers A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp(3)–sp(2) 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. WILEY-VCH Verlag 2014-07 2014-05-27 /pmc/articles/PMC4255755/ /pubmed/25505371 http://dx.doi.org/10.1002/ejoc.201402108 Text en © 2014 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2014 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Despiau, Carole F
Dominey, Andrew P
Harrowven, David C
Linclau, Bruno
Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title_full Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title_fullStr Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title_full_unstemmed Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title_short Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation
title_sort total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4255755/
https://www.ncbi.nlm.nih.gov/pubmed/25505371
http://dx.doi.org/10.1002/ejoc.201402108
work_keys_str_mv AT despiaucarolef totalsynthesisofparoxetinebydiastereoconvergentcobaltcatalysedarylation
AT domineyandrewp totalsynthesisofparoxetinebydiastereoconvergentcobaltcatalysedarylation
AT harrowvendavidc totalsynthesisofparoxetinebydiastereoconvergentcobaltcatalysedarylation
AT linclaubruno totalsynthesisofparoxetinebydiastereoconvergentcobaltcatalysedarylation

Ejemplares similares