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 L. Henry, 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 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.
Other articles related to "nitroaldol reaction, reaction":
... aldol addition product can be obtained in asymmetric synthesis by reaction of benzaldehyde with nitromethane and the a catalyst system consisting of a zinc triflate salt ... A diastereoselective variation of this reaction is depicted below ... yield employing Shisasaki's asymmetric Henry reaction as the key step ...
Famous quotes containing the word reaction:
“Children, randomly at first, hit upon something sooner or later that is their mothers and/or fathers Achilles heel, a kind of behavior that especially upsets, offends, irritates or embarrasses them. One parent dislikes name-calling, another teasing...another bathroom jokes. For the parents, this behavior my have ties back to their childhood, many have been something not allowed, forbidden, and when it appears in the child, it causes high-voltage reaction in the parent.”
—Ellen Galinsky (20th century)