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Related Reactions
Aldol Addition

Henry Reaction

The Henry 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.

If acidic 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

Recent Literature

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, 76, 484-491.

A New Catalyst for the Asymmetric Henry Reaction: Synthesis of β-Nitroethanols in High Enantiomeric Excess
J. D. White, S. Shaw, Org. Lett., 2012, 14, 6270-6273.

Practical Asymmetric Henry Reaction Catalyzed by a Chiral Diamine-Cu(OAc)2 Complex
T. Arai, M. Watanabe, A. Yanagisawa, Org. Lett., 2007, 9, 3595-3597.

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction
D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc., 2003, 125, 12692-12693.

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 Reaction
R. Ballini, G. Bosica, J. Org. Chem., 1997, 62, 425-427.

Hyperbranched Polyamines: Tunable Catalysts for the Henry Reaction
S. S. Ganesan, A. Ganesan, J. Kothandapani, Synlett, 2014, 25, 1847-1850.

Indium-Catalyzed Henry-Type Reaction of Aldehydes with Bromonitroalkanes
R. G. Soengas, A. M. S. Silva, Synlett, 2012, 23, 873-876.

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol
Y. Xia, M. Jiang, M. Liu, Y. Zhang, H. Qu, T. Xiong, H. Huang, D. Cheng, F. Chen, J. Org. Chem., 2021, 86, 11557-11570.

A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions
J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007, 72, 5451-5423.

Highly anti-Selective Asymmetric Nitro-Mannich Reactions Catalyzed by Bifunctional Amine-Thiourea-Bearing Multiple Hydrogen-Bonding Donors
C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc., 2008, 130, 8606-8607.

Dinuclear Zinc-AzePhenol Catalyzed Asymmetric Aza-Henry Reaction of N-Boc Imines and Nitroalkanes under Ambient Conditions
S. Liu, W.-C. Gao, Y.-H. Miao, M.-C. Wang, J. Org. Chem., 2019, 84, 2654-2659.

Aza-Henry Reaction of Ketoimines Catalyzed by Na2CO3: An Efficient Way to β-Nitroamines
L. Wang, C. Tan, X. Liu, X. Feng, Synlett, 2008, 2075-2077.

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.

Mechanistic Studies on the Michael Addition of Amines and Hydrazines To Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process
M. G. Kallitsakis, P. D. Tancini, M. Dixit, G. Mpourmpakis, I. N. Lykakis, J. Org. Chem., 2018, 83, 1176-1184.

Organic Chemistry Highlights
Enantioselective Aza-Henry and Aza-Michael Reactions