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Asymmetric hydrogenation of α,β-unsaturated sulfones by a rhodium/thiourea–bisphosphine complex

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Abstract

We herein report a method to synthesize chiral sulfone compounds. Catalyzed by a rhodium/thiourea–bisphosphine complex, various α,β-unsaturated sulfones were hydrogenated with high enantioselectivities. Kinetic studies suggested a first-order dependence of the reaction rate on the substrate concentration. Noticeable deactivation of the catalyst was observed in dichloromethane, which could be responsible for the eroded turnover number. The thiourea moiety was demonstrated to be important for high enantioselectivity and reactivity by control experiments.

Graphical abstract: Asymmetric hydrogenation of α,β-unsaturated sulfones by a rhodium/thiourea–bisphosphine complex

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Publication details

The article was received on 29 Nov 2018, accepted on 06 Mar 2019 and first published on 06 Mar 2019


Article type: Research Article
DOI: 10.1039/C8QO01291A
Citation: Org. Chem. Front., 2019, Advance Article

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    Asymmetric hydrogenation of α,β-unsaturated sulfones by a rhodium/thiourea–bisphosphine complex

    Y. Sun, J. Jiang, X. Guo, J. Wen and X. Zhang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01291A

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