Categories: C-N Bond Formation > Amines >
Synthesis of β-Amino ketones, esters, nitriles and related compounds
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Recent Literature
An efficient and very simple conjugate addition of aromatic and aliphatic
amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in
the presence of catalytic amount of silicon tetrachloride gave the corresponding
Michael adducts with very good yields.
N. Azizi, R. Baghi, H. Ghafuri, M. Boloutchian, M. Hashemi, Synlett, 2010,
379-382.
Ceric ammonium nitrate efficiently catalyzes the aza-Michael reaction of amines
with α,β-unsaturated carbonyl compounds in water to produce the corresponding
β-amino carbonyl compounds in very good yields under mild conditions. The
reaction is procedurally simple and offers limited chemoselectivity, as aromatic
amines were found to be unreactive.
R. Varala, N. Sreelatha, S. R. Adapa, Synlett, 2006,
1549-1553.
The
addition of primary and secondary amines to α,β-unsaturated esters,
nitriles, amides, and ketones mediated by solid lithium perchlorate gave the
corresponding saturated amines under solvent-free and environmentally
friendly conditions at room temperature.
N. Azizi,
M. R. Saidi, Tetrahedron, 2004, 60, 383-387.
Cellulose-supported copper(0) efficiently catalyzes aza-Michael reactions of
N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to
produce the corresponding β-amino compounds and N-substituted imidazoles in
excellent yields. The recovered catalyst can be used for several cycles with
consistent activity.
K. R. Reddy, N. S. Kumar, Synlett, 2006,
2246-2250.
CeCl3 • 7H2O/NaI supported on
neutral alumina (Al2O3) promotes heteroatom Michael
additions under solvent-free conditions. The CeCl3 • 7H2O/NaI/Al2O3
system works well for hetero-Michael additions of weak nucleophiles such as
imidazoles and carbamates to various acceptors.
G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E.
Torregiani, J. Org. Chem., 2005,
70, 169-174.
G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E.
Torregiani, J. Org. Chem., 2005,
70, 169-174.
A versatile RuCl3-catalyzed 1,4-conjugate addition of primary,
secondary and aromatic amines, thiols, and carbamates to α,β-unsaturated
compounds in poly(ethylene glycol) (PEG) provides the desired β-substituted
carbonyls in high yields. RuCl3-PEG offers low sensitivity toward moisture and
oxygen, high tolerance of different functional groups, and efficient
recyclability.
H. Zhang, Y. Zhang, L. Liu, H. Xu, Y. Wang, Synthesis, 2005,
2129-2136.
A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot
reaction sequence using commercially available catalysts at low catalyst
loadings gives β-hydroxy and β-amino esters in high yield and excellent
enantiopurity. The generation of quaternary stereocenters and application in
gram-scale synthesis were also realized, with no requirements of inert or
anhydrous reaction conditions.
H. Jiang, B. Gschwend, Ł. Albrecht, K. A. Jørgensen, Org. Lett., 2010,
12, 5052-5055.
The regio- and stereoselective aminochlorination of α,β-unsaturated ketones
with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and
CuOTf as catalyst provides an easy access to
vicinal haloamino ketones, with excellent regioselectivity and good yields.
Aromatic and aliphatic enones give opposite regioselectivity.
D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004,
3097-3101.
