1241391-02-5Relevant academic research and scientific papers
Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors
Kobayashi, Yusuke,Masakado, Sota,Takemoto, Yoshiji
supporting information, p. 693 - 697 (2018/01/17)
N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.
Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles
Miura, Tomoya,Biyajima, Tsuneaki,Fujii, Tetsuji,Murakami, Masahiro
supporting information; experimental part, p. 194 - 196 (2012/03/07)
N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.
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 (2013/08/23)
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.
Reductive aldol and mannich-type reactions of azetidin-3-ones promoted by titanium tetraiodide
Hata, Shingo,Fukuda, Daisuke,Hachiya, Iwao,Shimizu, Makoto
supporting information; experimental part, p. 473 - 477 (2010/08/23)
A convenient method is described for the generation and reaction of the enolates of aminoacetone equivalents, which uses the reduction of azetidin-3-one with titanium tetraiodide and subsequent reactions with electrophiles. This methodology provides a str
