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Enantioselective epoxidation of nonfunctionalized alkenes catalyzed by recyclable new homochiral bis-diamine-bridged bi-Mn(salen) complexes

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Abstract

Three new homochiral bis-diamine-bridged bi-Mn(salen) complexes were synthesized. Their catalysis on asymmetric epoxidation of α-methylstyrene, styrene and indene was studied with NaClO and m-CPBA as oxidants respectively. This homogeneous catalyst exhibited comparable catalytic activity and enantioselectivity to the Jacobsen’s catalyst in the asymmetric epoxidation of unfunctionalized olefins. Furthermore, the catalyst could be conveniently recovered and reused at least five times without significant losses of both activity and enantioselectivity. Specially, it also could be efficiently used in large-scale reactions with superior catalytic disposition being maintained at the same level, which provided the potential for the applications in industry. The effect of axial bases, temperature and solvent on activity and enantioselectivity of the catalytic system were also studied.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry Southwest University, Chongqing, 400715, China

    XueMei Huang, XiangKai Fu, ZiYong Jia, Qiang Miao & GuoMing Wang

  2. The Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing, 400715, China

    XueMei Huang, XiangKai Fu, ZiYong Jia, Qiang Miao & GuoMing Wang

  3. The Key Laboratory of Eco-environments in Three Gorges Reservoir Region Ministry of Education, Chongqing, 400715, China

    XiangKai Fu

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  1. XueMei Huang
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  2. XiangKai Fu
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Correspondence to XiangKai Fu.

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Huang, X., Fu, X., Jia, Z. et al. Enantioselective epoxidation of nonfunctionalized alkenes catalyzed by recyclable new homochiral bis-diamine-bridged bi-Mn(salen) complexes. Sci. China Chem. 56, 604–611 (2013). https://doi.org/10.1007/s11426-012-4829-x

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