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Synthesis of alkylamines

Name Reactions


Kulinkovich-de Meijere Reaction


Kulinkovich-Szymoniak Reaction


Petasis Reaction


Recent Literature


Various N-toluenesulfonylimines were successfully ethylated with diethylzinc in the presence of copper(II) ditriflate and a chiral amidophosphine ligand in toluene to give the corresponding N-toluenesulfonylamides in good yields and high enantioselectivity.
T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem., 2003, 59, 9655-9659.


The synthesis of free α-chiral amines by a one-pot multicomponent procedure involves the formation of N-diphenylphosphinoylimines from commercially available starting materials and the subsequent enantioselective addition of diakylzinc reagents using an air-stable precatalyst complex.
. Cote, A. B. Charette, J. Org. Chem., 2005, 70, 10864-10867.


A mild, versatile, copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides provides α-substituted amides or N-protected amines in a single step with the sole byproduct being indium trichloride.
D. A. Black, B. A. Arndtsen, Org. Lett., 2006, 8, 1991-1993.


Trialkylalanes undergo addition to imines in the presence of a catalytic amount of dichloro­dicyclopentadienylzirconium(IV). The reaction tolerates the presence of various functional groups. A possible reaction pathway is discussed.
C. Denhez, J.-L. Vasse, J. Szymoniak, Synthesis, 2005, 2075-2079.


A highly efficient three-component coupling reaction between thioformamides and organolithium and Grignard reagents was developed. The generality of the process has been demonstrated by using various combinations of reactants and reagents.
T. Murai, F. Asai, J. Am. Chem. Soc., 2007, 129, 780-781.


β-Functionalized sulfonamides were produced in good yields by the regioselective ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine (TMEDA).
S. Minakata, Y. Okada, Y. Oderaotoshi, M. Komatsu, Org. Lett., 2005, 7, 3509-3512.


The efficiency of the photoinduced radical addition of tertiary amines to olefinic double bonds is significantly enhanced and the stereoselectivity is influenced when thiocarbonyl compounds are added to the reaction mixture.
D. Harakat, J. Pesch, S. Marinkovic, N. Hoffmann, Org. Biomol. Chem., 2006, 4, 1202-1205.