Categories: C-C Bond Formation > Nitrogen-containing molecules > Synthesis of amines >
Synthesis of alkylamines
Name Reactions
Kulinkovich-de Meijere Reaction
Kulinkovich-Szymoniak 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.
