26020-23-5Relevant academic research and scientific papers
Synthesis of α-amino ketones and O-alkyloximes by titanium tetrahalide promoted ring-opening reaction of 2-mono-substituted azetidin-3-ones and their O-alkyloximes
Ariga, Shizuka,Hata, Shingo,Fukuda, Daisuke,Nishi, Takafumi,Hachiya, Iwao,Shimizu, Makoto
, p. 1187 - 1210 (2012)
Synthesis of α-amino ketones and O-alkyloximes has been developed by titanium tetrahalide-promoted ring-opening reactions of 2-mono-substituted azetidin-3-ones and their O-alkyloximes. Regarding the reductive ring-opening reactions of 2-mono-substituted azetidin-3-ones, an appropriate use of TiI 4 or TiI4-TiCl4 as a promoter gave α-amino ketones in good yields with high regioselectivities. In TiBr4-promoted ring-opening reactions, while use of 2-mono-substituted azetidin-3-ones as a substrate provided α-amino-α'-bromo ketones generated by the attack of the bromide anion at the less hindered site, those of 2-mono-substituted azetidin-3-one O-alkyloximes proceeded at the more hindered site to give α-amino-α'-bromo ketone O-alkyloximes in good yields.
