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Synthesis of Nitro compounds

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Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield within several minutes under ambient conditions. The preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.
A. J. Grenning, J.A. Tunge, Org. Lett., 2010, 12, 740-742.

A calcium vanadate apatite (VAp) acts as a high-performance heterogeneous base catalyst for various carbon-carbon bond-forming reactions such as Michael and aldol reactions in aqueous media. No vanadium leaching was detected and the catalyst was readily recycled with no loss of activity.
T. Hara, S. Kanai, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, J. Org. Chem., 2006, 71, 7455-7462.

A catalytic enantioselective direct conjugate addition of nitroalkanes to α,β-unsaturated aldehydes using diphenylprolinol silyl ether as an organocatalyst enables short syntheses of therapeutically useful compounds.
H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett., 2007, 9, 5307-5309.

C6'-OH cinchona alkaloid-catalyzed asymmetric nitroaldol reactions with α-ketoesters are highly efficient, operationally simple, and afford high enantioselectivity as well as good to excellent yield for a broad range of α-ketoesters.
H. Li, B. Wang. L. Deng, J. Am. Chem. Soc., 2006, 128, 732-733.

Racemic 1-nitroalkan-2-ols are obtained by reaction of bromonitromethane with a variety of aldehydes promoted by SmI₂. Chiral N,N-dibenzyl amino aldehydes afford the corresponding enantiopure 3-amino-1-nitroalkan-2-ols with good diastereoselectivity.
J. M. Concellón, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2006, 71, 7919-7922.

The Henry reaction can be performed under very mild reaction conditions in 0.025 M NaOH in the presence of cetyltrimethylammonium chloride as cationic surfactant. Short reaction times are required and both primary and secondary nitroalkanes give good results.
R. Ballini, G. Bosica, J. Org. Chem., 1997, 62, 425-427.

Electrochemically Induced Aza-Henry Reaction: A New, Mild, and Clean Synthesis of α-Nitroamines
L. Rossi, G. Bianchi, M. Feroci, A. Inesi, Synlett, 2007, 2505-2508.

A chiral bifunctional multiple hydrogen-bonding-donor amine-thiourea catalyzes a highly anti-selective and enantioselective nitro-Mannich reaction for a broad spectrum of substrates. Multiple hydrogen-bonding donors play a significant role in accelerating reactions and improving yields, diastereoselectivities, and enantioselectivities.
C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc., 2008, 130, 8606-8607.

In the presence of only 5 mol% Na₂CO₃, N-tosyl ketoimines can react with nitromethane to give β-nitroamines via aza-Henry reaction in very good yields in THF at room temperature.
L. Wang, C. Tan, X. Liu, X. Feng, Synlett, 2008, 2075-2077.

In a Michael addition of nitromethane to α,β-unsaturated aldehydes via iminium activation, a MeOPEG-supported, recyclable Jørgensen-Hayashi catalyst provides unchanged reactivity and selectivity as compared to the homogeneous catalyst. The immobilization enables a simple, column-free isolation of pure, sensitive aldehyde products and therefore may be useful for application in more complicated syntheses.
I. Mager, K. Zeitler, Org. Lett., 2010, 12, 1480-1483.

An N-spiro C₂-symmetric chiral quaternary ammonium bromide efficiently catalyzed the conjugate addition of various prochiral nitroalkanes to cyclic α,β-unsaturated ketones under solid-liquid phase-transfer conditions to afford the corresponding γ-nitro ketones in excellent yields with high levels of diastereo- and enantiocontrol.
T. Ooi, S. Takada, S. Fujioka, K. Maruoka, Org. Lett., 2005, 7, 5143-5146.

The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with excellent enantioselectivity and chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities.
S. Hanessian, Z. Shao, J. S. Warrier, Org. Lett., 2006, 8, 4787-4790.

The conversion of primary nitroalkanes into the corresponding α-nitro ketones readily proceeds using N-acylbenzotriazoles as acylation agents.
A. R. Katritzky, A. A. A. Abdel-Fattah, A. V. Gromova, R. Witek, P. J. Steel, J. Org. Chem., 2005, 70, 9211-9214.