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

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

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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

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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.