article published Constanza Terazzi author Anke Spannenberg author Jan von Langermann author Thomas Werner author 892710000-0001-9025-3244 35 department 2 department <jats:title>Abstract</jats:title><jats:p>The biocatalytic kinetic resolution of cyclic carbonates derived from glycerol is reported. A selection of 26 esterases and lipases was tested for the asymmetric hydrolysis of the model substrate (epichlorohydrin carbonate) in aqueous medium. Among them, Pig Liver Esterase and Novozym® 435 showed the best selectivity with <jats:italic>E</jats:italic>=38 and 49, respectively. Both enzymes were employed for the conversion of 12 glycerol derivatives under optimized conditions. The resolution of halogenated carbonates afforded the unconverted enantiomer in up to &gt;99 : 1 <jats:italic>er</jats:italic>. Furthermore, Novozym® 435 was successfully recycled 10 times without significant loss of activity. Upscaling and isolation of the chiral carbonate was also demonstrated. Subsequent conversion of this chiral building block allowed the direct one‐pot synthesis of (<jats:italic>S</jats:italic>)‐Guaifenesin, (<jats:italic>S</jats:italic>)‐Mephenesin and (<jats:italic>S</jats:italic>)‐Chlorphenesin in up to 89 % yield and 94 : 6 <jats:italic>er</jats:italic>.</jats:p> Wiley2023 eng T1T4CSSD 1867-3880 1867-389910.1002/cctc.202300917 1519 Terazzi, Constanza, Anke Spannenberg, Jan von Langermann, and Thomas Werner. “Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates.” <i>ChemCatChem</i> 15, no. 19 (2023). <a href="https://doi.org/10.1002/cctc.202300917">https://doi.org/10.1002/cctc.202300917</a>. C. Terazzi, A. Spannenberg, J. von Langermann, and T. Werner, “Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates,” <i>ChemCatChem</i>, vol. 15, no. 19, Art. no. e202300917, 2023, doi: <a href="https://doi.org/10.1002/cctc.202300917">10.1002/cctc.202300917</a>. Terazzi C, Spannenberg A, von Langermann J, Werner T. Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates. <i>ChemCatChem</i>. 2023;15(19). doi:<a href="https://doi.org/10.1002/cctc.202300917">10.1002/cctc.202300917</a> C. Terazzi, A. Spannenberg, J. von Langermann, T. Werner, ChemCatChem 15 (2023). Terazzi, Constanza, et al. “Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates.” <i>ChemCatChem</i>, vol. 15, no. 19, e202300917, Wiley, 2023, doi:<a href="https://doi.org/10.1002/cctc.202300917">10.1002/cctc.202300917</a>. @article{Terazzi_Spannenberg_von Langermann_Werner_2023, title={Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates}, volume={15}, DOI={<a href="https://doi.org/10.1002/cctc.202300917">10.1002/cctc.202300917</a>}, number={19e202300917}, journal={ChemCatChem}, publisher={Wiley}, author={Terazzi, Constanza and Spannenberg, Anke and von Langermann, Jan and Werner, Thomas}, year={2023} } Terazzi, C., Spannenberg, A., von Langermann, J., &#38; Werner, T. (2023). Chemoenzymatic Synthesis of Chiral Building Blocks Based on the Kinetic Resolution of Glycerol‐Derived Cyclic Carbonates. <i>ChemCatChem</i>, <i>15</i>(19), Article e202300917. <a href="https://doi.org/10.1002/cctc.202300917">https://doi.org/10.1002/cctc.202300917</a> 620962025-11-05T15:23:21Z2025-11-10T08:46:22Z