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Asymmetric Organocatalytic Direct C(sp2)[BOND]H/C(sp3)[BOND]H Oxidative Cross-Coupling by Chiral Iodine Reagents

Authors

  • Hua Wu,

    1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)
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  • Yu-Ping He,

    1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)
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  • Lue Xu,

    1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)
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  • Dong-Yang Zhang,

    1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)
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  • Prof. Liu-Zhu Gong

    Corresponding author
    1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)
    • Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (China)===

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  • We are grateful for financial support from NSFC (21232007, 21072181), MOST (973 project 2010CB833300), and the Ministry of Education. We thank Shi-Ming Zhou for the determination of absolute configuration.

Abstract

An asymmetric organocatalytic direct C[BOND]H/C[BOND]H oxidative coupling reaction of N1,N3-diphenylmalonamides has been well established by using chiral organoiodine compounds as catalysts, wherein four C[BOND]H bonds were stereoselectively functionalized to give structurally diverse spirooxindoles with high levels of enantioselectivity. More importantly, the findings indicated that chiral hypervalent organoiodine reagents can serve as alternative catalysts for the creation of enantioselective functionalization of inactive C[BOND]H bonds.

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