Differentiation of Epoxide Enantiomers in the Confined Spaces of an Homochiral Cu(II) Metal-Organic Framework by Kinetic Resolution |
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Authors: | Juanjo Cabezas-Giménez Dr. Vanesa Lillo Dr. José Luis Núñez-Rico Dr. M. Nieves Corella-Ochoa Dr. Jesús Jover Prof. Dr. José Ramón Galán-Mascarós Prof. Dr. Anton Vidal-Ferran |
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Affiliation: | 1. Institute of Chemical Research of Catalonia (ICIQ) and the Barcelona, Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona, Spain;2. Departament de Química Inorgànica i Orgànica, Universitat de Barcelona, C/Martí i Franqués 1–11, 08028 Barcelona, Spain |
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Abstract: | TAMOF-1 , a homochiral metal-organic framework (MOF) constructed from an amino acid derivative and Cu(II), was investigated as a heterogeneous catalyst in kinetic resolutions involving the ring opening of styrene oxide with a set of anilines. The branched products generated from the ring opening of styrene oxide with anilines and the unreacted epoxide were obtained with moderately high enantiomeric excesses. The linear product arising from the attack on the non-benzylic position of styrene oxide underwent a second kinetic resolution by reacting with the epoxide, resulting in an amplification of its final enantiomeric excess and a concomitant formation of an array of isomeric aminodiols. Computational studies confirmed the experimental results, providing a deep understanding of the whole process involving the two successive kinetic resolutions. Furthermore, TAMOF-1 activity was conserved after several catalytic cycles. The ring opening of a meso-epoxide with aniline catalyzed by TAMOF-1 was also studied and moderate enantioselectivities were obtained. |
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Keywords: | amino acids chirality epoxides kinetic resolution metal-organic framework |
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