A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks

[Image: see text] A telescoped continuous flow process is reported for the enantioselective synthesis of chiral precursors of 1-aryl-1,3-diols, intermediates in the synthesis of ezetimibe, dapoxetine, duloxetine, and atomoxetine. The two-step sequence consists of an asymmetric allylboration of readi...

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Autores principales: Maestro, Aitor, Nagy, Bence S., Ötvös, Sándor B., Kappe, C. Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629223/
https://www.ncbi.nlm.nih.gov/pubmed/37844195
http://dx.doi.org/10.1021/acs.joc.3c02040
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author Maestro, Aitor
Nagy, Bence S.
Ötvös, Sándor B.
Kappe, C. Oliver
author_facet Maestro, Aitor
Nagy, Bence S.
Ötvös, Sándor B.
Kappe, C. Oliver
author_sort Maestro, Aitor
collection PubMed
description [Image: see text] A telescoped continuous flow process is reported for the enantioselective synthesis of chiral precursors of 1-aryl-1,3-diols, intermediates in the synthesis of ezetimibe, dapoxetine, duloxetine, and atomoxetine. The two-step sequence consists of an asymmetric allylboration of readily available aldehydes using a polymer-supported chiral phosphoric acid catalyst to introduce asymmetry, followed by selective epoxidation of the resulting alkene. The process is highly stable for at least 7 h and represents a transition-metal free enantioselective approach to valuable 1-aryl-1,3-diols.
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spelling pubmed-106292232023-11-08 A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks Maestro, Aitor Nagy, Bence S. Ötvös, Sándor B. Kappe, C. Oliver J Org Chem [Image: see text] A telescoped continuous flow process is reported for the enantioselective synthesis of chiral precursors of 1-aryl-1,3-diols, intermediates in the synthesis of ezetimibe, dapoxetine, duloxetine, and atomoxetine. The two-step sequence consists of an asymmetric allylboration of readily available aldehydes using a polymer-supported chiral phosphoric acid catalyst to introduce asymmetry, followed by selective epoxidation of the resulting alkene. The process is highly stable for at least 7 h and represents a transition-metal free enantioselective approach to valuable 1-aryl-1,3-diols. American Chemical Society 2023-10-16 /pmc/articles/PMC10629223/ /pubmed/37844195 http://dx.doi.org/10.1021/acs.joc.3c02040 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Maestro, Aitor
Nagy, Bence S.
Ötvös, Sándor B.
Kappe, C. Oliver
A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title_full A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title_fullStr A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title_full_unstemmed A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title_short A Telescoped Continuous Flow Enantioselective Process for Accessing Intermediates of 1-Aryl-1,3-diols as Chiral Building Blocks
title_sort telescoped continuous flow enantioselective process for accessing intermediates of 1-aryl-1,3-diols as chiral building blocks
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629223/
https://www.ncbi.nlm.nih.gov/pubmed/37844195
http://dx.doi.org/10.1021/acs.joc.3c02040
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