- Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases
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The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.
- González-Granda, Sergio,Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor-Fernández, Vicente
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p. 520 - 527
(2019/11/16)
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- QUINAZOLINONE-TYPE COMPOUNDS AS CRTH2 ANTAGONISTS
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This application provides for compounds of the formula Formula I or a pharmaceutically acceptable salt thereof, wherein the individual variables are defined herein, as well as processes to prepare these compounds, pharmaceutical compositions comprising the same and their use in treating disease state associated with the CRTH2 receptor.
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- Aryl propargylic alcohols of high enantiomeric purity via lipase catalyzed resolutions
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A variety of substituted aryl propargylic alcohols were prepared via lipase catalyzed resolutions, the enantioselective hydrolysis of the corresponding esters being the method of choice.
- Waldinger, Claudia,Schneider, Manfred,Botta, Maurizio,Corelli, Federico,Summa, Vincenzo
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p. 1485 - 1488
(2007/10/03)
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