Categories: C-C Bond Formation > Nitrogen-containing molecules > Synthesis of amines >
Synthesis of allylamines
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Exposure of various N-arylsulfonyl aldimines to 2-butyne and hydrogen at
ambient pressure in the presence of a cationic iridium(I) catalyst modified by
BIPHEP provides reductive coupling products, allylic amines, in good yields as
single geometrical isomers. Nonsymmetric alkynes couple under standard
conditions with high levels of regioselection.
A. Barchuk, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc., 2007,
129, 8432-8433.
Using an iridium catalyst modified by (R)-Cl,MeO-BIPHEP, the
hydrogenating of alkynes in the presence of N-arylsulfonyl imines
delivers the corresponding allylic amines in highly optically enriched form.
This protocol circumvents the use of preformed vinyl metal reagents and is
applicable to aromatic, heteroaromatic, and aliphatic N-arylsulfonyl
aldimines.
M.-Y. Ngai, A. Barchuk, M. J. Krische, J. Am. Chem. Soc., 2007,
129, 12644-12645.
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.
A hydrovinylation of N-acetylenamines with ethylene is catalyzed by a
ruthenium hydride complex, RuHCl(CO)(PCy3)2, providing a
series of N-acetylamines with a quaternary carbon center with up to 99%
yield.
Q.-S. Wang, J.-H. Xie, W. Lei, S.-F. Zhu, L.-X. Wang, Q.-L. Zhou, Org. Lett., 2011,
13, 3388-3391.
Exposure of aromatic and aliphatic N-arylsulfonyl aldimines to equal
volumes of acetylene and hydrogen gas at 45°C and ambient pressure in the
presence of chirally modified cationic rhodium catalysts provides (Z)-dienyl
allylic amines in highly optically enriched form and as single geometrical
isomers.
E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007,
129, 7242-7243.
An efficient method for the preparation of various
2-aminomethyl-1,3-dienes was developed through the reaction of imines with an
organoindium reagent generated in situ from indium and 1,3-dibromo-2-butyne.
Three-component reactions of aldehydes, amines, and organoindium reagents gave
successful results in a one-pot process.
D. Seomoon, J. A, P. H. Lee, Org. Lett., 2009,
11, 2401-2404.
Catalytic Asymmetric Aza-Morita-Baylis-Hillman Reaction of Methyl Acrylate:
Role of a Bifunctional La(O-iPr)3/Linked-BINOL Complex
T. Yukawa, B. Seelig, Y. Xu, H. Morimoto, Y. Xu, H. Morimoto, S. Matsunaga,
A. Berkessel, M. Shibasaki, J. Am. Chem. Soc., 2010,
132, 11988-11992.
(S)-3-[2-(Diphenylphosphino)phenyl]BINOL is an efficient asymmetric
bifunctional organocatalyst for the aza-Morita-Baylis-Hillman reaction. The
Brønsted acid and Lewis base functionalities cooperate in substrate activation
to promote the reaction with high enantiocontrol.
K. Matsui, S. Takizawa, H. Sasai, Synlett,
2006, 761-765.
(S)-3-(N-Isopropyl-N-3-pyridinylaminomethyl)BINOL is an
efficient, bifunctional organocatalyst for the enantioselective
aza-Morita-Baylis-Hillman (aza-MBH) reaction. The acid-base-mediated
functionalities for the activation of the substrate and the fixing of
conformation of the organocatalyst are harmoniously performed to promote the
reaction with high enantiocontrol.
K. Matsui, S. Takizawa, H. Sasai, J. Am. Chem. Soc.,
2005,
127, 3680-3681.
Chiral Bifunctional Organocatalysts in Asymmetric Aza-Morita-Baylis-Hillman
Reactions of Ethyl (Arylimino)acetates with Methyl Vinyl Ketone and Ethyl Vinyl
Ketone
M. Shi, G.-N. Ma, J. Gao, J. Org. Chem., 2007,
72, 9779-9781.
Allylic N-sulfonylamines are synthesized in high yields and with high
regioselectivities by reaction of
N-sulfonylaziridines with excess dimethylsulfonium methylide.
D. M. Hodgson, M. J. Fleming, S. J. Stanway, Org. Lett., 2005,
7, 3295-3298.
Opening of the epoxide ring of enantiopure (2R,1'S)-2-(1-aminoalkyl)epoxides
with different organolithium compounds gave allylamines with total
selectivity and in high yields.
J. M. Concellon, J. R. Suarez, V. del Solar, Org. Lett.,
2006,
8, 349-351.
The reaction of various aromatic nitriles and conjugated alkenenitriles with 1.1
equiv of Ti(OiPr)4 and 2.2 equiv of EtMgBr followed by addition of a
Lewis acid gave 1-arylcyclopropylamines and 1-alkenylcyclopropylamines in good
yields.
P. Bertus, J. Szymoniak, J. Org. Chem., 2003,
68, 7133-7136.
