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HandWiki. Nitroaldol Reaction. Encyclopedia. Available online: https://encyclopedia.pub/entry/29193 (accessed on 23 September 2026).
HandWiki. Nitroaldol Reaction. Encyclopedia. Available at: https://encyclopedia.pub/entry/29193. Accessed September 23, 2026.
HandWiki. "Nitroaldol Reaction" Encyclopedia, https://encyclopedia.pub/entry/29193 (accessed September 23, 2026).
HandWiki. (2022, October 14). Nitroaldol Reaction. In Encyclopedia. https://encyclopedia.pub/entry/29193
HandWiki. "Nitroaldol Reaction." Encyclopedia. Web. 14 October, 2022.
Nitroaldol Reaction
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The content is sourced from: https://handwiki.org/wiki/Chemistry:Nitroaldol_reaction

The Henry Reaction (also referred to as the nitro-aldol reaction) is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834-1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-Nitro alcohols. This type of reaction is commonly referred to as a "nitro-aldol" reaction (nitroalkane, aldehyde, and alcohol) It is nearly analogous to the aldol reaction that had been discovered 23 years prior that couples two carbonyl compounds to form β-hydroxy carbonyl compounds known as "aldols" (aldehyde and alcohol). The Henry reaction is a useful technique in the area of organic chemistry due to the synthetic utility of its corresponding products, as they can be easily converted to other useful synthetic intermediates. These conversions include subsequent dehydration to yield nitroalkenes, oxidation of the secondary alcohol to yield α-nitro ketones, or reduction of the nitro group to yield β-amino alcohols. Many of these uses have been exemplified in the syntheses of various pharmaceuticals including the β-blocker (S)-propranolol, the HIV protease inhibitor Amprenavir (Vertex 478), and construction of the carbohydrate subunit of the anthracycline class of antibiotics, L-Acosamine. The synthetic scheme of the L-Acosamine synthesis can be found in the Examples section of this article.

aldol reaction s-propranolol nitroalkenes

References

  1. Reich, Hans. "Bordwell pKa table: "Nitroalkanes"". http://www.chem.wisc.edu/areas/reich/pkatable/. Retrieved 17 January 2016. 
  2. Matthews, Walter (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution". Journal of the American Chemical Society 97 (24): 7006. doi:10.1021/ja00857a010. http://pubs.acs.org/doi/abs/10.1021/ja00857a010. Retrieved 17 January 2016. 
  3. Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Burlington, MA: Elsevier Academic Press. pp. 202–203. ISBN 0-12-369483-3. 
  4. Noboro, Ono (2001). The Nitro Group in Organic Synthesis. New York, NY: Wiley-VCH. pp. 30–69. ISBN 0-471-31611-3. 
  5. Begona, L., Arrieta, A., Morao, I., Cossio, F.P. (1997). "Ab Initio Models for the Nitroaldol (Henry) Reaction". Chem. Eur. J. 3 (1): 20–28. doi:10.1002/chem.19970030105.  https://dx.doi.org/10.1002%2Fchem.19970030105
  6. Sasai, Hiroaki; Suzuki, Takeyuki; Arai, Shigeru; Arai, Takayoshi; Shibasaki, Masakatsu (1 May 1992). "Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactions". Journal of the American Chemical Society 114 (11): 4418–4420. doi:10.1021/ja00037a068.  https://dx.doi.org/10.1021%2Fja00037a068
  7. . List et al. described this process as the organocatalyst functioning as Lewis acid or base or Bronsted Acid or Base.
  8. Westermann, B. (2003). "Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1,2-diaminocarboxylic acids". Angew. Chem. Int. Ed. Engl. 42: 151–153. doi:10.1002/anie.200390071.  https://dx.doi.org/10.1002%2Fanie.200390071
  9. Seayad, J., List, B. (2005). "Asymmetric organocatalysis". Org. Biomol. Chem. 3 (5): 719–724. doi:10.1039/b415217b. PMID 15731852.  https://dx.doi.org/10.1039%2Fb415217b
  10. Luzzio, F.A. (2001). "The Henry Reaction: recent examples". Tetrahedron 57 (22): 915–945. doi:10.1002/chin.200122233.  https://dx.doi.org/10.1002%2Fchin.200122233
  11. Menzel, A., Ohrlein, R., Griesser, H., Wehner, V., Jager, V. (1999). "A Short Synthesis of L-Acosamine Based on Nitroaldol Addition (Henry Reaction). Analysis of the Key Step Concerning Solvent and Temperature Effects". Synthesis 9 (45): 1691–1702. doi:10.1002/chin.199945325.  https://dx.doi.org/10.1002%2Fchin.199945325
  12. Palomo, Claudio; Oiarbide, Mikel; Laso, Antonio (2005). "Enantioselective Henry Reactions under Dual Lewis Acid/Amine Catalysis Using Chiral Amino Alcohol Ligands". Angewandte Chemie 44 (25): 3881–3884. doi:10.1002/anie.200463075. http://www3.interscience.wiley.com/cgi-bin/abstract/110494368/ABSTRACT. 
  13. Alcaide, Benito; Almendros, Pedro; Luna, Amparo; Paz de Arriba, M.; Rosario Torresc, M. (2007). "Organocatalyzed diastereoselective Henry reaction of enantiopure 4-oxoazetidine-2-carbaldehydes". ARKIVOC 2007 (iv): 285–296. doi:10.3998/ark.5550190.0008.425. http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts/2007/JB-2021JP%20as%20published%20mainmanuscript.pdf. 
  14. Gogoi, N., Boruwa, J., Barua, N.C. (2005). "A total synthesis of (–)-bestatin using Shibasaki's asymmetric Henry reaction". Tetrahedron Letters 46 (44): 7581–7582. doi:10.1016/j.tetlet.2005.08.153.  https://dx.doi.org/10.1016%2Fj.tetlet.2005.08.153
  15. Marcelli, T., van der Haas, R., van Maarseveen, J.H., Hiemstra, H. (2006). "Asymmetric Organocatalytic Henry Reaction". Angew. Chem. Int. Ed. 45 (6): 929–931. doi:10.1002/anie.200503724.  https://dx.doi.org/10.1002%2Fanie.200503724
  16. Purkarthofer, T., Gruber, K., Gruber-Khadjawi, M., Waich, K., Skranc, W., Mink, D. and Griengl, H. (2006). "A Biocatalytic Henry Reaction—The Hydroxynitrile Lyase from Hevea brasiliensis Also Catalyzes Nitroaldol Reactions.". Angewandte Chemie 45: 3454–3456.. doi:10.1002/anie.200504230.  https://dx.doi.org/10.1002%2Fanie.200504230
  17. "Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system.". J. Biotechnol. 153: 153–9.. 2011. doi:10.1016/j.jbiotec.2011.03.011. PMID 21439333.  https://dx.doi.org/10.1016%2Fj.jbiotec.2011.03.011
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