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Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides

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Abstract

A highly diastereoselective and enantioselective Michael addition/desymmetrization reaction of maleimides with prochiral 3- substituted phthalides catalyzed by quinine-derived bifunctional thiourea was realized. A broad range of the 3,3′-disubstituted phthalides bearing vicinal quaternary-tertiary stereogenic centers were synthesized in moderate to good yields (up to 96%) with high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 96:4 er).

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21390400).

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Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, College of Chemistry, Nankai University, Tianjin, 300071, China

    Jie Wang, Xin Li & Jin-Pei Cheng

Authors
  1. Jie Wang
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  2. Xin Li
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  3. Jin-Pei Cheng
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Correspondence to Xin Li.

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Wang, J., Li, X. & Cheng, JP. Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides. Sci. China Chem. 62, 649–652 (2019). https://doi.org/10.1007/s11426-018-9393-2

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  • DOI: https://doi.org/10.1007/s11426-018-9393-2

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