Journal
ACS CATALYSIS
Volume 5, Issue 2, Pages 683-689Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs501629m
Keywords
diarylmethanol; dynamic kinetic resolution; lipase; ruthenium; catalysis
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Funding
- National Research Foundation of Korea [2012R1A1A2006595, 2012-007235]
- National Research Foundation of Korea [2012R1A1A2006595] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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We explored the kinetic resolution of 31 different diarylmethanols with an activated lipoprotein lipase (LPL-D1) which was about 3000-fold more active than its native counterpart in organic solvent. Most of the substrates tested were accepted by LPL-D1 with good to high enantioselectivity in the kinetic resolution. Next, we explored the dynamic kinetic resolutions (DKRs) of these substrates (24 out of 31) using LPL-D1 and a ruthenium-based racemization catalyst in combination, which provided satisfactory yields (71-96%) and high enantiopurities (90-99% cc). As an illustrative example for the synthetic applications of the DKR procedure, we synthesized L-cloperastine, an antitussive drug, from phenyl-(p-trimethylsilylphenyl)methanol via DKR.
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