54965-03-6Relevant academic research and scientific papers
Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates
Poeira, Diogo L.,Negr?o, Ana Cláudia R.,Faustino, Hélio,Coelho, Jaime A. S.,Gomes, Clara S. B.,Gois, Pedro M. P.,Marques, M. Manuel B.
supporting information, p. 776 - 781 (2022/01/20)
A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis and successfully employed in the α-amination of indanone-based β-ketoesters in up to 83% yield. Mechanistic studies indicate a substitution mechanism involving an electrophilic amine.
Zirconium Hydroaminoalkylation. An Alternative Disconnection for the Catalytic Synthesis of α-Arylated Primary Amines
Koperniku, Ana,Foth, Paul J.,Sammis, Glenn M.,Schafer, Laurel L.
supporting information, p. 18944 - 18948 (2019/12/04)
Primary amine products have been prepared using zirconium-catalyzed hydroaminoalkylation of alkenes with N-silylated benzylamine substrates. Catalysis using commercially available Zr(NMe2)4 affords an alternative disconnection to acc
A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality
Archer, Robert M.,Hutchby, Marc,Winn, Caroline L.,Fossey, John S.,Bull, Steven D.
, p. 8838 - 8847 (2015/10/20)
Aza-conjugate addition of the lithium anion of N-trimethylsilyl-p-methoxybenzylamine to tert-butyl enoate acceptors, in the presence of a stoichiometric amount of enantiopure 1,2-dimethoxy-1,2-diphenylethane and excess trimethylsilyl chloride, affords ter
Organosilicon synthesis of isocyanates: II. Synthesis of aliphatic, carbocyclic, and fatty-aromatic isocyanates
Lebedev,Lebedeva,Sheludyakov,Ovcharuk,Kovaleva,Ustinova
, p. 469 - 477 (2008/02/07)
Silylation of a series of aliphatic, carbocyclic, and fatty-aromatic amines gave the corresponding silyl derivatives whose yield depended on the electronic and steric structure of the substrate and the nature of the silylating agent. The yield of isocyanates obtained by phosgenation of the silyl derivatives under mild conditions decreased in going from aliphatic amines to benzylamines and rose as the length of the alkyl chain in fatty-aromatic amines extended. The most convenient procedure for the synthesis of low-boiling alkyl isocyanates was found to be based on the transformation of amines or ammonium salts into silyl or silyl silyl-carabamates, followed by pyrolysis of the latter in the presence of trichloro(phenyl)silane. Pleiades Publishing, Inc., 2006.
