Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Nitro compounds
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Recent Literature
Me-DuPHOS monoxide is a very effective ligand in the enantioselective
copper-catalyzed enantioselective addition of dialkylzinc reagents to
β-nitroalkenes offering high yields of nitroalkanes, broad and complementary
substrate scope, and high enantioselectivities.
A. Côté, V. N. G. Lindsay, A. B. Charette, Org. Lett., 2007,
9, 85-87.
Copper-catalyzed conjugate addition of dialkylzing reagents to acyclic
nitroalkenes using a chiral phosphoramidite ligand gave products in
enantioselectivities up to 98%. Routes to (functionalized) 2-amino
aldehydes, acids, and alcohols are described.
A. Duursma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc., 2003,
125, 3700-3701.
An efficient and highly enantioselective conjugate addition of alkylzinc
reagents to various cyclic nitroalkenes is promoted in the presence of 0.5-5
mol % (CuOTf)2·C6H6 and 1-10 mol % of
chiral amino acid-based phosphine ligands at 0°C in toluene. Depending on
the reaction conditions used, either the nitro or the corresponding
α-substituted ketone product can be accessed.
C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc., 2002,
124, 8192-8193.
A simple organocatalyst provided access to Michael adducts of the addition of
nitroalkenes to aldehydes with very high diastereo- and enantioselectivity and a
broad range of β-substitution patterns. Almost equimolar amounts of
the aldehyde donor can be employed.
C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. Int. Ed., 2006,
45, 5984-5987.
Pyrrolidine-based chiral ionic liquids are highly efficient organocatalysts
for Michael additions of a broad range of michael donors (both ketones and
aldehydes) to nitroolefins with high yields, excellent enantioselectivities,
and very good diastereoselectivities. The ionic liquid moiety not only acts
as a tag to facilitate recycling but functions also as an efficient
chiral-induction group.
S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, J.-P. Cheng, Angew. Chem. Int.
Ed., 2006,
45, 3093-3097.
A fluorous (S)-pyrrolidine sulfonamide organocatalyst promotes highly
enantio- and diastereoselective Michael addition reactions of ketones and
aldehydes with nitroolefins in water. The organocatalyst is conveniently
recovered from the reaction mixtures by fluorous solid-phase extraction and
can be reused.
L. Zu, J. Wang, H. Li, W. Wang, Org. Lett.,
2006,
8, 3077-3079.
An axially chiral guanidine catalyst facilitated the highly enantioselective
1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of
conjugated nitroalkenes and showed extremely high catalytic activity.
M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc.,
2006,
128, 1454-1455.
A new bifunctional catalyst bearing a thiourea moiety and an amino group was
highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl
compounds to nitroolefins to afford the Michael adducts with high enantio-
and diastereoselectivity.
T. Okino, Y. Hoashi, T. Fukukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc.,
2005,
7, 119-125.
A Ni(II)-(bis)diamine-catalyzed, highly enantioselective Michael addition of
substituted and unsubstituted malonates and β-ketoesters to nitroalkenes
bearing aromatic and aliphatic residues has been developed.
D. A. Evans, D. Seidel, J. Am. Chem. Soc.,
2005,
127, 9958-9959.
