53693-47-3Relevant academic research and scientific papers
One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C?H Imination
Comito, Robert J.,Ghosh, Subrata K.,Hu, Mengnan
supporting information, p. 17601 - 17608 (2021/11/03)
The direct replacement of sp3 C?H bonds with simple amine units (?NH2) remains synthetically challenging, although primary aliphatic amines are ubiquitous in medicinal chemistry and natural product synthesis. We report a mild and selective protocol for preparing primary and secondary aliphatic amines in a single pot, based on intermolecular sp3 C?H imination. The first C?H imination of diverse alkanes, this method shows useful site-selectivity within substrates bearing multiple sp3 C?H bonds. Furthermore, this reaction tolerates polar functional groups relevant for complex molecule synthesis, highlighted in the synthesis of amine pharmaceuticals and amination of natural products. We characterize a unique C?H imination mechanism based on radical rebound to an iminyl radical, supported by kinetic isotope effects, stereoablation, resubmission, and computational modeling. This work constitutes a selective method for complex amine synthesis and a new mechanistic platform for C?H amination.
Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst
Chang, Yejin,Cao, Min,Chan, Jessica Z.,Zhao, Cunyuan,Wang, Yuankai,Yang, Rose,Wasa, Masayuki
supporting information, p. 2441 - 2455 (2021/02/16)
We disclose a catalytic method for β-C(sp3)-H functionalization of N-alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C6F5)3, and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C-H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described.
Design, Synthesis, and Evaluation of 5′-Diphenyl Nucleoside Analogues as Inhibitors of the Plasmodium falciparum dUTPase
Hampton, Shahienaz E.,Baragana, Beatriz,Schipani, Alessandro,Bosch-Navarrete, Cristina,Musso-Buendia, J. Alexander,Recio, Eliseo,Kaiser, Marcel,Whittingham, Jean L.,Roberts, Shirley M.,Shevtsov, Mikhail,Brannigan, James A.,Kahnberg, Pia,Brun, Reto,Wilson, Keith S.,Gonzalez-Pacanowska, Dolores,Johansson, Nils Gunnar,Gilbert, Ian H.
, p. 1816 - 1831 (2012/07/03)
Deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase) is a potential drug target for malaria. We previously reported some 5′-tritylated deoxyuridine analogues (both cyclic and acyclic) as selective inhibitors of the Plasmodium falciparum dUTPase. Mod
Monoalkylation of primary amines and N-sulfinylamides
García Ruano, José Luis,Parra, Alejandro,Alemán, José,Yuste, Francisco,Mastranzo, Virginia M.
supporting information; experimental part, p. 404 - 406 (2009/05/06)
An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described. The Royal Society of Chemistry.
