Literature DB >> 25485210

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

Nicholas A White1, Kerem E Ozboya1, Darrin M Flanigan1, Tomislav Rovis1.   

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 δ-lactams.

Entities:  

Year:  2014        PMID： 25485210      PMCID： PMC4251551          DOI： 10.1002/ajoc.201402031

Source DB:  PubMed          Journal:  Asian J Org Chem        ISSN： 2193-5807            Impact factor:   3.319


  33 in total

1.  Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine.

Authors:  Masato Ito; Ayaka Sakaguchi; Chika Kobayashi; Takao Ikariya
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

2.  Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine.

Authors:  Peter S Hynes; Paul A Stupple; Darren J Dixon
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

Review 3.  Paroxetine. An update of its pharmacology and therapeutic use in depression and a review of its use in other disorders.

Authors:  N S Gunasekara; S Noble; P Benfield
Journal:  Drugs       Date:  1998-01       Impact factor: 9.546

4.  Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products.

Authors:  Carmen Escolano; Mercedes Amat; Joan Bosch
Journal:  Chemistry       Date:  2006-11-06       Impact factor: 5.236

5.  Highly diastereoselective and enantioselective carbon-carbon bond formations in conjugate additions of lithiated N-Boc allylamines to nitroalkenes: enantioselective synthesis of 3,4- and 3,4,5-substituted piperidines including (-)-paroxetine.

Authors:  T A Johnson; M D Curtis; P Beak
Journal:  J Am Chem Soc       Date:  2001-02-07       Impact factor: 15.419

6.  Improved synthesis of paroxetine hydrochloride propan-2-ol solvate through one of metabolites in humans, and characterization of the solvate crystals.

Authors:  K Sugi; N Itaya; T Katsura; M Igi; S Yamazaki; T Ishibashi; T Yamaoka; Y Kawada; Y Tagami; M Otsuki; T Ohshima
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-04       Impact factor: 1.645

7.  A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Authors:  Puneet Kumar; Janis Louie
Journal:  Org Lett       Date:  2012-04-02       Impact factor: 6.005

Review 8.  Paroxetine: a review.

Authors:  M Bourin; P Chue; Y Guillon
Journal:  CNS Drug Rev       Date:  2001

9.  Synthesis of (-)-paroxetine via enantioselective phase-transfer catalytic monoalkylation of malonamide ester.

Authors:  Mi-Hyun Kim; Yohan Park; Byeong-Seon Jeong; Hyeung-Geun Park; Sang-Sup Jew
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

Review 10.  Chromone and flavonoid alkaloids: occurrence and bioactivity.

Authors:  Shahriar Khadem; Robin J Marles
Journal:  Molecules       Date:  2011-12-27       Impact factor: 4.411
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  2 in total

1.  Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Authors:  Tao Shu; Qijian Ni; Xiaoxiao Song; Kun Zhao; Tianyu Wu; Rakesh Puttreddy; Kari Rissanen; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2016-01-11       Impact factor: 6.222

2.  Enantioselective N-heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums.

Authors:  Darrin M Flanigan; Tomislav Rovis
Journal:  Chem Sci       Date:  2017-08-03       Impact factor: 9.825
  2 in total

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