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Synthesis of Nitro compounds

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Henry Reaction


Recent Literature


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.


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.


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.