キハラ ノブヒロ   Kihara Nobuhiro
  木原 伸浩
   所属   神奈川大学  理学部 化学科
   職種   教授
言語種別 英語
発行・発表の年月 2018/02
形態種別 学術雑誌
査読 査読あり
標題 Synthesis of α-Aminocarbonyl Compounds via Hetero Diels­Alder Reaction
執筆形態 共著
掲載誌名 Chem. Lett.
掲載区分国内
出版社・発行元 Chemical Society of Japan
巻・号・頁 47(2),pp.144-147
著者・共著者 Masayoshi Sakurai, Nobuhiro Kihara, Nobuhiro Watanabe, Yoshihiro Ikari, and Toshikazu Takata
概要 A synthetic route to α-aminoketone derivatives via the hetero Diels-Alder reaction is described. Diacylhydrazine was oxidized by tert-butyl hypochlorite in the presence of pyridine. After evaporation, the hetero Diels-Alder reaction with diene was carried out without isolation of the azodicarbonyl compound. Quantitative hetero Diels-Alder reaction was possible with 1 equivalent of diene when Hf(OTf)4 or AgOTf was used as the catalyst. The N-N bond of the product was cleaved by SmI2-reduction in the presence of tert-BuOH in THF. Further, ozonolysis of the C=C double bond afforded the α-aminoketone derivative in excellent yield.