898282-31-0Relevant academic research and scientific papers
Nitrosobenzene-mediated C-C bond cleavage reactions and spectral observation of an oxazetidin-4-one ring system
Payette, Joshua N.,Yamamoto, Hisashi
supporting information; experimental part, p. 12276 - 12278 (2009/02/05)
While bond formation processes have traditionally garnered the attention of the chemical community, methods facilitating bond breaking remain relatively undeveloped. We report a novel, transition-metal-free oxidative C-C bond cleavage process for a broad range of ester and dicarbonyl compounds involving carbanion addition to nitrosobenzene. ReactIR experiments on the nitrosobenzene-mediated oxidative decarboxylation of esters indicate the reaction proceeds via fragmentation of a previously unobserved oxazetidin-4-one heterocycle, characterized by an intense IR stretching frequency at 1846 cm-1. These mechanistic studies have allowed further expansion of this protocol to ketone cleavage reactions of a diverse array of β-ketoester and 1,3-diketone substrates. The conceptual and mechanistic insights offered by this study are likely to provide a platform for further development of bond-breaking methodologies. Copyright
Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile
Wu, Pengcheng,Wang, Zhouyu,Cheng, Mounuo,Zhou, Li,Sun, Jian
experimental part, p. 11304 - 11312 (2009/04/06)
l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the
Rationally-designed S-chiral bissulfinamides as highly enantioselective organocatalysts for reduction of ketimines
Pei, Dong,Zhang, Yu,Wei, Siyu,Wang, Meng,Sun, Jian
supporting information; experimental part, p. 619 - 623 (2009/04/21)
We recently reported the first example of S-chiral organocatalysts, that are highly efficient and enantioselective in substoichometric amounts, and which use a chiral monosulfinamide group as Lewis base to activate trichlorosilane (HSiCl3) to reduce N-arylketimines. Aplausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl 3 prompted us to design S-chiral bissulfinamides as new catalysts. We herein describe our findings that an easily prepared S-chiral bissulfinamide bearing a five-methylene linkage not only inherited the excellent substrate generality from the monosulfinamide catalysts, but also exhibited further improved enantioselectivity.
