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    Optically Pure C1-Symmetric Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Asymmetric Olefin Metathesis

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    optically pure.pdf
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    Description:
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    Type
    Article
    Authors
    Morvan, Jennifer cc
    Vermersch, François
    Zhang, Ziyun
    Falivene, Laura cc
    Vives, Thomas cc
    Dorcet, Vincent
    Roisnel, Thierry
    Crévisy, Christophe cc
    Cavallo, Luigi cc
    Vanthuyne, Nicolas cc
    Bertrand, Guy cc
    Jazzar, Rodolphe cc
    Mauduit, Marc cc
    KAUST Department
    Chemical Science Program
    Physical Science and Engineering (PSE) Division
    KAUST Catalysis Center (KCC)
    Date
    2020-11-13
    Embargo End Date
    2021-11-13
    Permanent link to this record
    http://hdl.handle.net/10754/665952
    
    Metadata
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    Abstract
    An expedient access to the first optically pure ruthenium complexes containing C1-symmetric cyclic (alkyl)(amino)carbene ligands is reported. They demonstrate excellent catalytic performances in asymmetric olefin metathesis with high enantioselectivities (up to 92% ee). Preliminary mechanistic insights provided by density functional theory models highlight the origin of the enantioselectivity.
    Citation
    Morvan, J., Vermersch, F., Zhang, Z., Falivene, L., Vives, T., Dorcet, V., … Mauduit, M. (2020). Optically Pure C1-Symmetric Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Asymmetric Olefin Metathesis. Journal of the American Chemical Society. doi:10.1021/jacs.0c10705
    Sponsors
    We are grateful to the CNRS, the Ecole Nationale Superieure ́de Chimie de Rennes, the Aix-Marseille Universite, and the ́ University of California San Diego. This work was supported by the Region Bretagne (ARED 2018 “Biometa” N° 601, grant to J.M.), the Agence Nationale de la Recherche (ANR-19- CE07-0017 ChiCAAC, R.J. and M.M.), and the U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program, under Award DESC0009376 (G.B.). Umicore AG & Co. is acknowledged for a generous gift of ruthenium complexes. M.M. and T.V. thank Shimadzu and Chiral Technology for their support in the separation of chiral molecules by Supercritical Fluid Chromatography (SFC) technology. For computer time, this research used the resources of the KAUST Supercomputing Laboratory (KSL) at KAUST.
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/jacs.0c10705
    PubMed ID
    33185429
    Additional Links
    https://pubs.acs.org/doi/10.1021/jacs.0c10705
    Relations
    Is Supplemented By:
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 1942929: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC236S48. DOI: 10.5517/ccdc.csd.cc236s48 Handle: 10754/669182
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 1973067: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC2474BW. DOI: 10.5517/ccdc.csd.cc2474bw Handle: 10754/669183
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 1941527: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC2359XJ. DOI: 10.5517/ccdc.csd.cc2359xj Handle: 10754/669184
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 2026393: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC260MJD. DOI: 10.5517/ccdc.csd.cc260mjd Handle: 10754/669185
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 2026394: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC260MKF. DOI: 10.5517/ccdc.csd.cc260mkf Handle: 10754/669186
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 2033131: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC267MWZ. DOI: 10.5517/ccdc.csd.cc267mwz Handle: 10754/669187
    • [Dataset]
      Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, & Mauduit, Marc. (2020). CCDC 2033132: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC267MX0. DOI: 10.5517/ccdc.csd.cc267mx0 Handle: 10754/669188
    ae974a485f413a2113503eed53cd6c53
    10.1021/jacs.0c10705
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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