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Issue 65, 2016
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Catalytic enantioselective epoxidation of nitroalkenes

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Abstract

Nitroepoxides are potentially exploitable as synthons with vicinal electrophilic centers. Nevertheless, although advances have been made in the field, enantioselective epoxidation of nitroalkenes is still a challenging process. Herein we show a convenient procedure for the preparation of optically active nitroepoxides in high enantiomeric excess and high chemical yield. The kinetic data of the best catalyst have been examined using computational methods based on DFT calculations. Interestingly, the results demonstrate that the enantioselectivity of the epoxidation of nitroalkenes by this kind of catalyst is not only kinetically but also thermodynamically controlled.

Graphical abstract: Catalytic enantioselective epoxidation of nitroalkenes

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Publication details

The article was received on 28 Apr 2016, accepted on 15 Jul 2016 and first published on 18 Jul 2016


Article type: Communication
DOI: 10.1039/C6CC03539F
Citation: Chem. Commun., 2016,52, 10060-10063
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    Catalytic enantioselective epoxidation of nitroalkenes

    A. Vidal-Albalat, K. Świderek, J. Izquierdo, S. Rodríguez, V. Moliner and F. V. González, Chem. Commun., 2016, 52, 10060
    DOI: 10.1039/C6CC03539F

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