Multigram-scale flow synthesis of the chiral key intermediate of (−)-paroxetine enabled by solvent-free heterogeneous organocatalysis-Reference-Cited by-同舟云学术

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

Published:2019 Issue:48 Volume:10 Page:11141-11146
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Ötvös Sándor B.¹²³⁴⁵^ORCID,Pericàs Miquel A.⁶⁷⁸⁹¹⁰^ORCID,Kappe C. Oliver¹²³⁴⁵^ORCID

Affiliation:

1. Institute of Chemistry

2. University of Graz

3. NAWI Graz

4. A-8010 Graz

5. Austria

6. Institute of Chemical Research of Catalonia (ICIQ)

7. The Barcelona Institute of Science and Technology (BIST)

8. E-43007 Tarragona

9. Spain

10. Departament de Química Inorgànica i Orgànica

Abstract

The continuous flow synthesis of the chiral key intermediate of (−)-paroxetine is demonstrated via a solvent-free organocatalytic conjugate addition followed by a telescoped reductive amination–lactamization–amide/ester reduction sequence.

Funder

Austrian Science Fund

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/SC/C9SC04752B

Reference61 articles.

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3. R. Vardanyan and V.Hruby , in Synthesis of Best-Seller Drugs , Academic Press , Boston , 2016 , ch. 7, pp. 119–121

4. Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

5. Palladium-Catalyzed Asymmetric Allylic Allylation of Racemic Morita-Baylis-Hillman Adducts

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