328073-57-0Relevant academic research and scientific papers
Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids
Cartwright, Kaitie C.,Lang, Simon B.,Tunge, Jon A.
, p. 2933 - 2940 (2019/03/26)
Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.
Decarboxylative Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual Catalysis
Cartwright, Kaitie C.,Tunge, Jon A.
, p. 11801 - 11806 (2018/12/11)
A dual-catalytic strategy for the synthesis of enamides and enecarbamates directly from easily accessible and inexpensive amino acids has been realized. This mild and efficient protocol makes use of an organic photoredox catalyst and a cobaloxime catalyst to achieve decarboxylative elimination using hydrogen evolution to drive the oxidation. Thus, the reaction occurs without a stoichiometric oxidant or the forcing conditions previously employed in attempts to achieve similar eliminations.
Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: Enantioselective arylation of enecarbamates
Hashimoto, Takuya,Nakatsu, Hiroki,Takiguchi, Yuka,Maruoka, Keiji
, p. 16010 - 16013 (2013/11/19)
The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Bronsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.
Enamides accessed from aminothioesters via a Pd(0)-catalyzed decarbonylative/β-hydride elimination sequence
Min, Geanna K.,Hernandez, Dacil,Lindhardt, Anders T.,Skrydstrup, Troels
supporting information; experimental part, p. 4716 - 4719 (2010/12/25)
A facile synthesis of various enamides from aminothioesters via a palladium(0)-catalyzed decarbonylation/β-hydride elimination is reported. This protocol was applied to mercaptopyridyl C-terminal modified peptides for the generation of enamides without ep
Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral Bronsted acid
Terada, Masahiro,Sorimachi, Keiichi
, p. 292 - 293 (2008/04/18)
We present the first enantioselective catalysis of the Friedel-Crafts reaction via activation of electron-rich multiple bonds by a chiral Bronsted acid. The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the
