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Asymmetric N[BOND]H Insertion Reaction Cooperatively Catalyzed by Rhodium and Chiral Spiro Phosphoric Acids

Authors

  • Bin Xu,

    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • Prof. Shou-Fei Zhu,

    Corresponding author
    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
    • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • Xiu-Lan Xie,

    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • Jun-Jie Shen,

    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • Prof. Qi-Lin Zhou

    Corresponding author
    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
    • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • We thank the National Natural Science Foundation of China and the National Basic Research Program of China (2011CB808600), and the “111” project (B06005) of the Ministry of Education of China for financial support.

Abstract

original image

So near so SPA: Achiral dirhodium(II) carboxylates and chiral spiro phosphoric acids (SPA) cooperatively catalyzed asymmetric N[BOND]H insertion reactions with high enantioselectivity, high yields, and fast reaction rates at low catalyst loading (see scheme; Boc=tert-butyloxycarbonyl, TPA=triphenylacetyl). Chiral spiro phosphoric acid assisted asymmetric proton transfer is proposed as the chiral induction step.

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