Strecker-Type Reaction of Nitrones Using Cyanohydrin

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  • Sakai Takahiro
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Soeta Takahiro
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Inomata Katsuhiko
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Ukaji Yutaka
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University

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Strecker-type reaction of nitrones using acetone cyanohydrin as a cyanide source was developed. By treating nitrones with acetone cyanohydrin in the presence of n-BuMgCl, transcyanation from the cyanohydrin to the nitrones smoothly proceeded in THF at 35 °C. The amount of n-BuMgCl could be reduced to 0.2 equiv to give the corresponding α-cyanohydroxylamines in up to 98% yields.

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