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Stereoselective Enzymatic Reduction of 1,4-Diaryl-1,4-Diones to the Corresponding Diols Employing Alcohol Dehydrogenases

1
Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Spain
2
Departamento de Química Orgánica, Universidad de Sevilla, c/Profesor García González, 41012 Sevilla, Spain
*
Authors to whom correspondence should be addressed.
Catalysts 2018, 8(4), 150; https://doi.org/10.3390/catal8040150
Received: 18 January 2018 / Revised: 27 March 2018 / Accepted: 3 April 2018 / Published: 6 April 2018
(This article belongs to the Special Issue Enzyme-Mediated Stereoselective Synthesis)
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Abstract

Due to the steric hindrance of the starting prochiral ketones, the preparation of chiral 1,4-diaryl-1,4-diols through the asymmetric hydrogen transfer reaction has been mainly restricted to the use of metal-based catalysts, oxazaborolidines, or organocatalysts. Herein, we demonstrated the versatility of oxidoreductases, finding overexpressed alcohol dehydrogenase from Ralstonia sp. (E. coli/RasADH) as the most active and stereoselective biocatalyst. Thus, the preparation of a set of 1,4-diaryl-1,4-diols bearing different pattern substitutions in the aromatic ring was achieved with complete diastereo- and enantioselectivity under mild reaction conditions. View Full-Text
Keywords: alcohol dehydrogenases; asymmetric synthesis; bioreduction; 1,4-diols; diketones alcohol dehydrogenases; asymmetric synthesis; bioreduction; 1,4-diols; diketones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Mourelle-Insua, Á.; De Gonzalo, G.; Lavandera, I.; Gotor-Fernández, V. Stereoselective Enzymatic Reduction of 1,4-Diaryl-1,4-Diones to the Corresponding Diols Employing Alcohol Dehydrogenases. Catalysts 2018, 8, 150.

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