Literature DB >> 20499863

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

Mi-Hyun Kim1, Yohan Park, Byeong-Seon Jeong, Hyeung-Geun Park, Sang-Sup Jew.   

Abstract

A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.

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Year:  2010        PMID： 20499863     DOI： 10.1021/ol100928v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

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

Authors:  Nicholas A White; Kerem E Ozboya; Darrin M Flanigan; Tomislav Rovis
Journal:  Asian J Org Chem       Date:  2014-04       Impact factor: 3.319

2.  Pharmacological use of a novel scaffold, anomeric N,N-diarylamino tetrahydropyran: molecular similarity search, chemocentric target profiling, and experimental evidence.

Authors:  Arramshetti Venkanna; Oh Wook Kwon; Sualiha Afzal; Cheongyun Jang; Kyo Hee Cho; Dharmendra K Yadav; Kang Kim; Hyeung-Geun Park; Kwang-Hoon Chun; Sun Yeou Kim; Mi-Hyun Kim
Journal:  Sci Rep       Date:  2017-10-02       Impact factor: 4.379

3.  Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis.

Authors:  Sándor B Ötvös; Miquel A Pericàs; C Oliver Kappe
Journal:  Chem Sci       Date:  2019-10-18       Impact factor: 9.825
  3 in total

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