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A Telescoped Continuous Flow Enantioselective Process to Access Chiral Intermediates of Atomoxetine, Dapoxetine, Duloxetine and Ezetimibe

22 August 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

continuous flow
asymmetric catalysis
organocatalysis
chiral phosphoric acid

Supplementary materials

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Experimental procedures and characterization data
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Experimental procedures and characterization data
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Version History

Aug 22, 2023 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-93llx
D O I: 10.26434/chemrxiv-2023-93llx [opens in a new tab]

Funding

Austrian Science Fund
P 34397-N

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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