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Total Synthesis of (±)‐Paroxetine by Diastereoconvergent Cobalt‐Catalysed Arylation
Author(s) -
Despiau Carole F.,
Dominey Andrew P.,
Harrowven David C.,
Linclau Bruno
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402108
Subject(s) - chemistry , piperidine , stereoselectivity , cobalt , cyclohexane , substrate (aquarium) , stereochemistry , ring (chemistry) , total synthesis , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , oceanography , geology
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.