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Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones

Authors

  • Prof. Dr. Bing Han,

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
    • State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Xiu-Long Yang,

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Dr. Ran Fang,

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Prof. Dr. Wei Yu,

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Chao Wang,

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Xiao-Yong Duan,

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • Shuai Liu

    1. State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
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  • We are grateful for financial support from the NSFC (Nos. 20902040 and J1103307), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1138), the 111 Project, and the Fundamental Research Funds for the Central Universities (lzujbky-2012-61).

Abstract

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Mit Diethyl-DEAD und TEMPO gelang die intramolekulare Addition von Oximradikalen an C[DOUBLE BOND]C-Bindungen zur Bildung von 4,5-Dihydroisoxazolen. Die Reaktion verläuft über eine 5-exo-trig-Cyclisierung unter C-O-Kupplung. γ,δ-Ungesättigte Ketoxime reagierten ebenfalls und ergaben cyclische Nitrone. Die Reaktion ist ein metallfreier Ansatz für die vicinale Difunktionalisierung nichtaktivierter Alkene.

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