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A flash thermal racemization protocol for the chemoenzymatic dynamic kinetic resolution and stereoinversion of chiral amines
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takle-et-al-2023-a-flash-thermal-racemization-protocol-for-the-chemoenzymatic-dynamic-kinetic-resolution-and.pdf | Published version | 1.8 MB | Adobe PDF | View/Open |
Title: | A flash thermal racemization protocol for the chemoenzymatic dynamic kinetic resolution and stereoinversion of chiral amines |
Authors: | Takle, MJ Deadman, BJ Hellgardt, K Dickhaut, J Wieja, A Hii, KKM |
Item Type: | Journal Article |
Abstract: | A highly practical and effective ‘Flash Thermal Racemization’ (FTR) protocol was developed in continuous flow, without needing a base or a H donor. This can be integrated with an enzyme to enable the chemoenzymatic kinetic resolution of primary amines to be achieved in a more atom-efficient manner without additives. An unprecedented space-time yield of up to 1362 μmol mL–1 h–1 can be achieved for the dynamic kinetic resolution of 1-aminoindane, which is at least 10 times more productive than previously reported, and up to 1700-fold more productive when the Pd catalyst loading is taken into account. With a slight modification, the flow reactor system can also be used to convert an optically active amine to its opposite enantiomer. |
Issue Date: | 18-Aug-2023 |
Date of Acceptance: | 26-Jul-2023 |
URI: | http://hdl.handle.net/10044/1/109976 |
DOI: | 10.1021/acscatal.3c02859 |
ISSN: | 2155-5435 |
Publisher: | American Chemical Society |
Start Page: | 10541 |
End Page: | 10546 |
Journal / Book Title: | ACS Catalysis |
Volume: | 13 |
Issue: | 16 |
Copyright Statement: | Copyright © 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0. |
Publication Status: | Published |
Online Publication Date: | 2023-07-28 |
Appears in Collections: | Chemistry Catalysis and Advanced Materials Chemical Engineering Faculty of Natural Sciences |
This item is licensed under a Creative Commons License