Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435 |
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| Authors: | Nan Young Jeon Sung-Jin Ko Han-Young Kang Yeon Soo Lee |
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| Institution: | a Bioorganic Science Division, Korea Research Institute of Chemical Technology, Daejeon 305-600, Republic of Korea
b Department of Chemistry and Institute of Basic Science, Chungbuk National University, Chungbuk 361-763, Republic of Korea |
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| Abstract: | Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate. |
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| Keywords: | Novozym 435 Kinetic resolution Alkyl lactate rac-Lactide Alkyl O-lactyllactate |
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