Consecutive Oxygen-based Oxidations Convert Amines to a-Cyanoepoxides

    • Dmitry B. Ushakova
    • Kerry Gilmore*a
    • Peter H. Seeberger*a,b
    • aMax Planck Institute of Colloids and Interfaces, Potsdam, Germany
    • bInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Berlin, Germany

    Tri- or tetrasubstituted α-cyanoepoxides can be rapidly prepared from unactivated amines and malononitrile or methyl cyanoacetate when singlet oxygen, produced in a continuous-flow photoreactor, serves as an oxidant and in situ peroxide source. The hydrogen peroxide generated in amine oxidation epoxidizes an electron deficient olefin intermediate, formed by deaminative Mannich coupling. The corresponding α,α-dicyano- or α-cyano-α-esterepoxides were obtained in good yields (43–82%).

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