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      Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut

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          Abstract

          The two-step flow asymmetric synthesis of chiral γ-nitrobutyric acids as key intermediates of the GABA analogues baclofen, phenibut, and fluorophenibut is reported on a multigram scale. The telescoped process comprises an enantioselective Michael-type addition facilitated by a polystyrene-supported heterogeneous organocatalyst under neat conditions followed by in situ-generated performic acid-mediated aldehyde oxidation. Simple access to valuable optically active substances is provided with key advances in terms of productivity and sustainability compared to those of previous batch approaches.

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          Author and article information

          Journal
          Org Lett
          Org Lett
          ol
          orlef7
          Organic Letters
          American Chemical Society
          1523-7060
          1523-7052
          07 October 2020
          16 October 2020
          : 22
          : 20
          : 8122-8126
          Affiliations
          []Institute of Chemistry, University of Graz , NAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria
          []Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center Pharmaceutical Engineering GmbH (RCPE) , Inffeldgasse 13, A-8010 Graz, Austria
          [§ ]Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology (BIST) , Av. Països Catalans 16, E-43007 Tarragona, Spain
          []Departament de Química Inorgànica i Orgànica, Universitat de Barcelona (UB) , E-08028 Barcelona, Spain
          Author notes
          Article
          10.1021/acs.orglett.0c03100
          7573919
          33026815
          b15eb255-98f9-4451-92e0-dc912368be52
          © 2020 American Chemical Society

          This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.

          History
          : 15 September 2020
          Categories
          Letter
          Custom metadata
          ol0c03100
          ol0c03100

          Organic & Biomolecular chemistry
          Organic & Biomolecular chemistry

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