Reaction is a base-catalyzed C-C bond-forming reaction between
nitroalkanes and aldehydes or ketones. It is similar to the
Aldol Addition, and also referred to
as the Nitro Aldol Reaction.
protons are available (i.e. when R = H), the products tend to eliminate
water to give nitroalkenes. Therefore, only small amounts of base should
be used if the isolation of the β-hydroxy nitro-compounds is desired.
Mechanism of the Henry Reaction
A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction
Using a Bis(sulfonamide)-Diamine Ligand
W. Jin, X. Li, B. Wan, J. Org. Chem., 2011,
A New Catalyst for the Asymmetric Henry Reaction: Synthesis of
β-Nitroethanols in High Enantiomeric Excess
J. D. White, S. Shaw, Org. Lett., 2012,
Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)2 Complex
T. Arai, M. Watanabe, A. Yanagisawa, Org. Lett., 2007,
A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry
D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc.,
Enantioselective Nitroaldol Reaction of α-Ketoesters Catalyzed by Cinchona Alkaloids
H. Li, B. Wang. L. Deng, J. Am. Chem. Soc., 2006, 128, 732-733.
Nitroaldol Reaction in Aqueous Media: An Important Improvement of the Henry
R. Ballini, G. Bosica, J. Org. Chem., 1997, 62, 425-427.
Indium-Catalyzed Henry-Type Reaction of Aldehydes with Bromonitroalkanes
R. G. Soengas, A. M. S. Silva, Synlett, 2012, 23,
A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under
J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007,