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

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 aldeh...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-11, Vol.88 (21), p.15523-15529
Main Authors: Maestro, Aitor, Nagy, Bence S., Ötvös, Sándor B., Kappe, C. Oliver
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02040