Geometrically Selective Synthesis of (<i>E</i>)-Enamides via Radical Allylation of Alkyl Halides with α-Aminoallylic Stannanes

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  • Kensuke Suzuki
    Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
  • Yoshihiro Nishimoto
    Frontier Research Base for Young Researchers, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
  • Makoto Yasuda
    Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

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説明

The reaction of α-(carbonylamino)allylic stannanes and alkyl halides using Et3B as a radical initiator selectively afforded (E)-enamides. A radical mechanism enables the E selectivity, which is unusual in a reaction using α-aminoallylic metals. In addition, this reaction system achieved a wide degree of functional group tolerance and an efficient chiral transfer reaction.

収録刊行物

  • Organic Letters

    Organic Letters 21 (17), 6589-6592, 2019-07-05

    American Chemical Society (ACS)

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