1190830-34-2Relevant academic research and scientific papers
A mild hydration of nitriles catalysed by copper(ii) acetate
Marcé, Patricia,Lynch, James,Blacker, A. John,Williams, Jonathan M. J.
supporting information, p. 1436 - 1438 (2016/01/25)
A simple, mild and general procedure for the hydration of nitriles to amides using copper as catalyst and promoted by N,N-diethylhydroxylamine is described. The reaction can be conducted in water at low temperature in short reaction times. This new procedure allows amides to be obtained from a wide range of substrates in excellent yields.
Managing highly coordinative substrates in asymmetric catalysis: A catalytic asymmetric amination with a lanthanum-based ternary catalyst
Mashiko, Tomoyuki,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information; experimental part, p. 14990 - 14999 (2010/01/30)
Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)3·6H2O, (R)-3a and H-D-Val-OtBu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading. Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)3· 6H2O/(R)-3a/H-D-Val-OtBu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted α-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to >99% yield and >99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.
