Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation
Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation
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
4335-4341
Despiau, Carole F.
03159972-4a40-414a-8101-fdb46f085a98
Dominey, Andrew P.
5d300fe5-2982-4710-beb5-cedd2139417a
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
July 2014
Despiau, Carole F.
03159972-4a40-414a-8101-fdb46f085a98
Dominey, Andrew P.
5d300fe5-2982-4710-beb5-cedd2139417a
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Despiau, Carole F., Dominey, Andrew P., Harrowven, David C. and Linclau, Bruno
(2014)
Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation.
European Journal of Organic Chemistry, 2014 (20), .
(doi:10.1002/ejoc.201402108).
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
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e-pub ahead of print date: 27 May 2014
Published date: July 2014
Identifiers
Local EPrints ID: 367007
URI: http://eprints.soton.ac.uk/id/eprint/367007
ISSN: 1434-193X
PURE UUID: ad874d74-bf9d-4f06-8e96-53b8ebfdc577
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Date deposited: 18 Jul 2014 09:12
Last modified: 15 Mar 2024 03:05
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Author:
Carole F. Despiau
Author:
Andrew P. Dominey
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