Chemoenzymatic Synthesis of Enantiopure Amino Alcohols from Simple Methyl Ketones

This study highlights the straight‐forward synthesis of substituted 1,2‐amino alcohols from simple and readily available aromatic methyl ketones. Starting from acetophenone derivatives, the straight‐forward synthesis strategy involved an initial bromination of the alpha‐positioned methyl group in th...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-09, Vol.26 (34)
Main Authors: Neuburger, Jan Eric, Gazizova, Alina, Tiedemann, Sven, von Langermann, Jan
Format: Article
Language:English
Subjects:
Acetophenone
Alcohols
Bromination
Ketones
Synthesis
Transaminases
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Summary:This study highlights the straight‐forward synthesis of substituted 1,2‐amino alcohols from simple and readily available aromatic methyl ketones. Starting from acetophenone derivatives, the straight‐forward synthesis strategy involved an initial bromination of the alpha‐positioned methyl group in the first step, followed by a simple hydrolysis to the hydroxyketone (2‐hydroxyacetophenone). The hydroxylated intermediate was subsequently converted from Silicibacter pomeroyi to the final 1,2‐amino alcohol by using the transaminase. The transaminase‐catalyzed reaction proceeded with yields up to 62 % and always excellent enantiomeric excess of >99 %. Interestingly, the keto‐enol‐tautomerism of the hydroxyl ketone yields an unexpected amino alcohol isomer.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201471