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

[Image: see text] 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 poly...

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Autores principales: Ötvös, Sándor B., Llanes, Patricia, Pericàs, Miquel A., Kappe, C. Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7573919/
https://www.ncbi.nlm.nih.gov/pubmed/33026815
http://dx.doi.org/10.1021/acs.orglett.0c03100
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author Ötvös, Sándor B.
Llanes, Patricia
Pericàs, Miquel A.
Kappe, C. Oliver
author_facet Ötvös, Sándor B.
Llanes, Patricia
Pericàs, Miquel A.
Kappe, C. Oliver
author_sort Ötvös, Sándor B.
collection PubMed
description [Image: see text] 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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spelling pubmed-75739192020-10-20 Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut Ötvös, Sándor B. Llanes, Patricia Pericàs, Miquel A. Kappe, C. Oliver Org Lett [Image: see text] 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. American Chemical Society 2020-10-07 2020-10-16 /pmc/articles/PMC7573919/ /pubmed/33026815 http://dx.doi.org/10.1021/acs.orglett.0c03100 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Ötvös, Sándor B.
Llanes, Patricia
Pericàs, Miquel A.
Kappe, C. Oliver
Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title_full Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title_fullStr Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title_full_unstemmed Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title_short Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut
title_sort telescoped continuous flow synthesis of optically active γ-nitrobutyric acids as key intermediates of baclofen, phenibut, and fluorophenibut
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7573919/
https://www.ncbi.nlm.nih.gov/pubmed/33026815
http://dx.doi.org/10.1021/acs.orglett.0c03100
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