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

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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

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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:
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    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
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Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)