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Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

ABSTRACT: A concise enantioselective synthesis of (-)-paroxetine (Paxil) and (-)-femoxetine has been achieved. Key to these syntheses is a N-heterocyclic carbene catalyzed homoenolate addition to a nitroalkene followed by in situ reduction of the nitro-group to rapidly access ?-lactams.

SUBMITTER: White NA 

PROVIDER: S-EPMC4251551 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via <i>N</i>-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

White Nicholas A NA   Ozboya Kerem E KE   Flanigan Darrin M DM   Rovis Tomislav T  

Asian journal of organic chemistry 20140401 4

A concise enantioselective synthesis of (-)-paroxetine (<i>Paxil</i>) and (-)-femoxetine has been achieved. Key to these syntheses is a <i>N</i>-heterocyclic carbene catalyzed homoenolate addition to a nitroalkene followed by in situ reduction of the nitro-group to rapidly access δ-lactams. ...[more]

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