Enzymatic reduction of α-substituted ketones with concomitant dynamic kinetic resolution

[Display omitted] •Enzymatic reduction of racemic α-substituted ketones and simultaneous dynamic kinetic resolution.•Stereoselective preparation of homochiral α-substituted chiral alcohols.•Reductions of N-protected α-amino ketones provided N-protected α-amino alcohols in high de and ee.•Choice of b...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2016-11, Vol.133, p.20-26
Main Authors: Hanson, Ronald L., Guo, Zhiwei, González-Bobes, Francisco, Fenster, Michaël D.B., Goswami, Animesh
Format: Article
Language:English
Subjects:
Chiral alcohols
Dynamic kinetic resolution
Enzymatic reduction
α-Substituted ketones
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Summary:[Display omitted] •Enzymatic reduction of racemic α-substituted ketones and simultaneous dynamic kinetic resolution.•Stereoselective preparation of homochiral α-substituted chiral alcohols.•Reductions of N-protected α-amino ketones provided N-protected α-amino alcohols in high de and ee.•Choice of buffer is crucial for the reduction of an α-methyl ketone to the corresponding alcohol in high deand ee.•Glucose dehydrogenase is acting as a ketoreductase. Racemic α-substituted ketones were converted to the corresponding chiral alcohols with high diastereo- and enantioselectivities using enzymatic reduction with concomitant dynamic kinetic resolution. Reductions of N-protected α-amino ketones by microorganisms and commercial enzymes provided N-protected α-amino alcohols. Choice of buffer was found to be a crucial factor for the successful reduction and simultaneous dynamic resolution of an α-methyl ketone to the corresponding chiral alcohol.
ISSN:1381-1177
1873-3158
DOI:10.1016/j.molcatb.2016.07.008