21906-05-8Relevant academic research and scientific papers
Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins
Méndez-Sánchez, Daniel,Mangas-Sánchez, Juan,Busto, Eduardo,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 122 - 131 (2016)
Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.
