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Enantioselective Morita–Baylis–Hillman Reaction of Acrylates with Nitrobenzaldehydes Promoted by the Bifunctional Ferrocene-Based Phosphinothiourea Organocatalysts

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Abstract

A series of ferrocene-based bifunctional phosphinothiourea organocatalysts were synthesized and applied to the enantioselective Morita–Baylis–Hillman reaction of acrylates with nitrobenzaldehydes, giving the desired products in up to 99.7 % ee. The strong electron-withdrawing effect of nitro group and hydrogen bonding interactions between the thiourea moiety of catalyst and aldehyde might be crucial during the enantio-controlling process.

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Acknowledgments

We thank the National Natural Science Foundation of China (21472240, 21272271) for financial support.

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    Authors and Affiliations

    1. Department of Medicinal Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, 710032, China

      Chuang Li, Yang Lei, Hui Chen, Shao-Yu Guan, Ru Jiang & Wei-Ping Chen

    2. Department of Pharmacy, The 60th Central Hospital of the PLA, Dali, 671003, China

      Peng-Fei Ma

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    1. Chuang Li
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    Correspondence to Ru Jiang or Wei-Ping Chen.

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    Chuang Li and Peng-Fei Ma have contributed equally to this work.

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    Li, C., Ma, PF., Lei, Y. et al. Enantioselective Morita–Baylis–Hillman Reaction of Acrylates with Nitrobenzaldehydes Promoted by the Bifunctional Ferrocene-Based Phosphinothiourea Organocatalysts. Catal Lett 146, 1429–1434 (2016). https://doi.org/10.1007/s10562-016-1759-9

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    • DOI: https://doi.org/10.1007/s10562-016-1759-9

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