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Diastereoconvergent Synthesis of (–)‐Paroxetine
Author(s) -
ChamorroArenas Delfino,
Fuentes Lilia,
Quintero Leticia,
CruzGregorio Silvano,
Höpfl Herbert,
SartilloPiscil Fernando
Publication year - 2017
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.201700658
Subject(s) - chemistry , epoxide , diastereomer , regioselectivity , ring (chemistry) , absolute configuration , stereochemistry , catalysis , stereoselectivity , epoxy , organic chemistry
A diastereoconvergent approach to (–)‐paroxetine from diastereomeric 3,4‐epoxy‐2‐piperidones is reported. For this synthesis, a regioselective and stereodivergent Cu I ‐catalyzed epoxide‐ring‐opening reaction of epoxyamide precursors to give the 4‐(4‐fluorophenyl)‐2‐piperidone skeleton with the correct absolute configuration is crucial. Using CuBr · SMe 2 as a catalyst, the epoxide‐ring‐opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.