 | This article may be too technical for most readers to understand. (May 2019) |
| Henry reaction | |
|---|---|
| Named after | Louis Henry |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | henry-reaction |
| RSC ontology ID | RXNO:0000086 |
The Henry 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.[1][2][3] This type of reaction is also referred to as a nitroaldol 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).[2][4] 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,[5][6] the HIV protease inhibitor Amprenavir (Vertex 478), and construction of the carbohydrate subunit of the anthracycline class of antibiotics, L-Acosamine.[6] The synthetic scheme of the L-Acosamine synthesis can be found in the Examples section of this article.
- ^ Henry, Louis (1895). "Formation synthétique d'alcools nitrés" [Synthetic formation of nitrated alcohols]. Comptes rendus. 120: 1265–1268.
- ^ a b Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Burlington, MA: Elsevier Academic Press. pp. 202–203. ISBN 978-0-12-369483-6.
- ^ Noboro, Ono (2001). The Nitro Group in Organic Synthesis. New York, NY: Wiley-VCH. pp. 30–69. ISBN 978-0-471-31611-4.
- ^ Wurtz, M.A. (1872). "Sur un aldéhyde-alcool". Bull. Soc. Chim. Fr. 17: 436–442.
- ^ Sasai, H., Suzuki, T., Itoh, N., Arai, S., Shibasaki, M. (1993). "Catalytic Asymmetric Nitroaldol Reaction: an efficient synthesis of (s) propranolol using the lanthenum binaphthol complex". Tetrahedron Letters. 34 (52): 855–858. doi:10.1016/0040-4039(93)89031-K.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b Luzzio, F.A. (2001). "The Henry Reaction: recent examples". Tetrahedron. 57 (22): 915–945. doi:10.1002/chin.200122233.