A Flash Thermal Racemization Protocol for the Chemoenzymatic Dynamic Kinetic Resolution and Stereoinversion of Chiral Amines

A Flash Thermal Racemization Protocol for the Chemoenzymatic Dynamic Kinetic Resolution and Stereoinversion of Chiral Amines

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 w...

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Veröffentlicht in:ACS catalysis 2023-08, Vol.13 (16), p.10541-10546
Hauptverfasser: Takle, Matthew J., Deadman, Benjamin J., Hellgardt, Klaus, Dickhaut, Joachim, Wieja, Andy, Hii, King Kuok Mimi
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container_end_page 10546
container_issue 16
container_start_page 10541
container_title ACS catalysis
container_volume 13
creator Takle, Matthew J.
Deadman, Benjamin J.
Hellgardt, Klaus
Dickhaut, Joachim
Wieja, Andy
Hii, King Kuok Mimi
description 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.
doi_str_mv 10.1021/acscatal.3c02859
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title A Flash Thermal Racemization Protocol for the Chemoenzymatic Dynamic Kinetic Resolution and Stereoinversion of Chiral Amines
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