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

dc.contributor.authorMorvan, Jennifer
dc.contributor.authorVermersch, François
dc.contributor.authorZhang, Ziyun
dc.contributor.authorFalivene, Laura
dc.contributor.authorVives, Thomas
dc.contributor.authorDorcet, Vincent
dc.contributor.authorRoisnel, Thierry
dc.contributor.authorCrévisy, Christophe
dc.contributor.authorCavallo, Luigi
dc.contributor.authorVanthuyne, Nicolas
dc.contributor.authorBertrand, Guy
dc.contributor.authorJazzar, Rodolphe
dc.contributor.authorMauduit, Marc
dc.date.accessioned2020-11-15T13:49:00Z
dc.date.available2020-11-15T13:49:00Z
dc.date.issued2020-11-13
dc.identifier.citationMorvan, 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
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.pmid33185429
dc.identifier.doi10.1021/jacs.0c10705
dc.identifier.urihttp://hdl.handle.net/10754/665952
dc.description.abstractAn 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.
dc.description.sponsorshipWe 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.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/jacs.0c10705
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/jacs.0c10705.
dc.titleOptically Pure C1-Symmetric Cyclic(alkyl)(amino)carbene Ruthenium Complexes for Asymmetric Olefin Metathesis
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.identifier.journalJournal of the American Chemical Society
dc.rights.embargodate2021-11-13
dc.eprint.versionPost-print
dc.contributor.institutionUniversité de Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR UMR 6226, F-35000Rennes, France
dc.contributor.institutionUCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, United States
dc.contributor.institutionDipartimento di Chimica e Biologia, Università di Salerno, Via Papa Paolo Giovanni II, 84100 Fisiciano, Italy
dc.contributor.institutionAix Marseille Université, CNRS, Centrale Marseille, iSm2, Marseille 13397, France
kaust.personZhang, Ziyun
kaust.personCavallo, Luigi
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc236s48
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc2474bw
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc2359xj
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc260mjd
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc260mkf
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc267mwz
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc267mx0
refterms.dateFOA2020-11-18T11:37:13Z
display.relations<b>Is Supplemented By:</b><br/> <ul><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 1942929: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC236S48. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc236s48" >10.5517/ccdc.csd.cc236s48</a> Handle: <a href="http://hdl.handle.net/10754/669182" >10754/669182</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 1973067: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC2474BW. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc2474bw" >10.5517/ccdc.csd.cc2474bw</a> Handle: <a href="http://hdl.handle.net/10754/669183" >10754/669183</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 1941527: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC2359XJ. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc2359xj" >10.5517/ccdc.csd.cc2359xj</a> Handle: <a href="http://hdl.handle.net/10754/669184" >10754/669184</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 2026393: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC260MJD. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc260mjd" >10.5517/ccdc.csd.cc260mjd</a> Handle: <a href="http://hdl.handle.net/10754/669185" >10754/669185</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 2026394: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC260MKF. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc260mkf" >10.5517/ccdc.csd.cc260mkf</a> Handle: <a href="http://hdl.handle.net/10754/669186" >10754/669186</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 2033131: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC267MWZ. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc267mwz" >10.5517/ccdc.csd.cc267mwz</a> Handle: <a href="http://hdl.handle.net/10754/669187" >10754/669187</a></a></li><li><i>[Dataset]</i> <br/> Morvan, Jennifer, Vermersch, François, Zhang, Ziyun, Falivene, Laura, Vives, Thomas, Dorcet, Vincent, Roisnel, Thierry, Crévisy, Christophe, Cavallo, Luigi, Vanthuyne, Nicolas, Bertrand, Guy, Jazzar, Rodolphe, &amp; Mauduit, Marc. (2020). <i>CCDC 2033132: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC267MX0. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc267mx0" >10.5517/ccdc.csd.cc267mx0</a> Handle: <a href="http://hdl.handle.net/10754/669188" >10754/669188</a></a></li></ul>
kaust.acknowledged.supportUnitKAUST Supercomputing Laboratory (KSL)


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