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

Catalysts

Gonzalo de Gonzalo¹  Vicente Gotor-Fernández²  Ángela Mourelle-Insua²  Iván Lavandera² 

[1] Departamento de Química Orgánica, Universidad de Sevilla, c/Profesor García González, 41012 Sevilla, Spain;Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Spain;

关键词: alcohol dehydrogenases;    asymmetric synthesis;    bioreduction;    1,4-diols;    diketones;   

DOI  :  10.3390/catal8040150

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown