Diastereoconvergent Synthesis of (–)‐Paroxetine | Zendy

ChamorroArenas Delfino | Zendy; Fuentes Lilia | Zendy; Quintero Leticia | Zendy; CruzGregorio Silvano | Zendy; Höpfl Herbert | Zendy; SartilloPiscil Fernando | Zendy

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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.

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