10465-74-4Relevant academic research and scientific papers
Synthesis of α-aminocarbonyl compounds via hetero dielsalder reaction
Sakurai, Masayoshi,Kihara, Nobuhiro,Watanabe, Nobuhiro,Ikari, Yoshihiro,Takata, Toshikazu
supporting information, p. 144 - 147 (2018/01/01)
A synthetic route to α-aminoketone derivatives via a hetero DielsAlder reaction is described. Diacylhydrazine was oxidized by tert-butyl hypochlorite in the presence of pyridine. After evaporation, the hetero DielsAlder reaction with diene was carried out without isolation of the azodicarbonyl compound. Quantitative hetero DielsAlder reaction was possible with 1 equivalent of diene when Hf(OTf)4 or AgOTf was used as the catalyst. The NN 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.
