AI Article Synopsis
- Different ketoreductases (KREDs) were used for the selective reduction of various 1-aryl-2-(azaaryl)ethanones, producing high-yield secondary alcohols with enantiomeric excess greater than 99%.
- The absolute configurations of the resulting optically active alcohols were determined using modified Mosher and Kelly methods, evaluating the effects of the Mosher phenyl ring and the azaaryl ring.
- The process also successfully synthesized the active amine lanicemine from one of the secondary alcohols, demonstrating their practical use in further chemical applications.
Article Abstract
Different ketoreductases (KREDs) have been used to promote a highly selective reduction of several 1-aryl-2-(azaaryl)ethanones (azaaryl = pyridinyl, quinolin-2-yl), the corresponding secondary alcohols being obtained with very high yields and enantiomeric excesses (ee > 99%). The absolute configuration of each optically active alcohol has been assigned by means of modified Mosher and Kelly methods, two shielding effects being evaluated: (1) the Mosher phenyl ring effect on the azaaryl protons and (2) the one of the azaaryl ring on the Mosher methoxy group. In addition, the biologically active amine lanicemine has been synthesized from (R)-1-phenyl-2-(pyridin-2-yl)ethanol, thus proving the utility of the secondary alcohols here prepared.
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| http://dx.doi.org/10.1039/c9ob01616c | DOI Listing |
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