A flash thermal racemization protocol for the chemoenzymatic dynamic kinetic resolution and stereoinversion of chiral amines
Author(s)
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.
Date Issued
2023-08-18
Date Acceptance
2023-07-26
Citation
ACS Catalysis, 2023, 13 (16), pp.10541-10546
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.
CC-BY 4.0.
License URL
Identifier
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:001039575000001&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=a2bf6146997ec60c407a63945d4e92bb
Subjects
ALKALINE-EARTH SUPPORTS
CATALYST
Chemistry
Chemistry, Physical
chiral amines
continuous flow synthesis
design-of-experiment optimization
dynamic kinetic resolution
EFFICIENT
flash thermal racemization
PALLADIUM
PD
Physical Sciences
Science & Technology
stereochemical inversion
Publication Status
Published
Date Publish Online
2023-07-28