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Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid

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Abstract

A catalytic enantioselective three-component Ugi reaction was developed. SPINOL-derived phosphoric acid with bulky 2,4,6-tricyclohexylphenyl groups at the 6,6′ positions was found to be the best catalyst to afford α-amino amide derivatives in good to excellent yields (62% to 99%) and enantiocontrol (81% to >99% enantiomeric excess). This asymmetric reaction was applicable well to an array of aliphatic aldehydes. The gram-scale synthesis, modification of dapsone, and enantioselective synthesis of (R)-Lacosamide underline the general utility of this methodology Influence of dihedral angles and substituents of the chiral phosphoric acids on the enantioselectivity was also discussed in this article.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21825105, 21772081), Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries (JCYJ20170412151701379, KQJSCX20170328153203), Special Funds for the Cultivation of Guangdong College Students’ Scientific and Technological Innovation (PDJH2019C467).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, 150001, China

    Jian Zhang

  2. Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055, China

    Jian Zhang, Yi-Yan Wang, He Sun, Shao-Yu Li, Shao-Hua Xiang & Bin Tan

  3. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, 518055, China

    Shao-Yu Li & Shao-Hua Xiang

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  1. Jian Zhang
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  2. Yi-Yan Wang
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  3. He Sun
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  5. Shao-Hua Xiang
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  6. Bin Tan
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Correspondence to Bin Tan.

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Zhang, J., Wang, YY., Sun, H. et al. Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid. Sci. China Chem. 63, 47–54 (2020). https://doi.org/10.1007/s11426-019-9606-2

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  • DOI: https://doi.org/10.1007/s11426-019-9606-2

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