Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Nitro compounds
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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.

