The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst.[1] While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter.[2] The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors. Unlike 1,3-dicarbonyls, which are easily accessed through the Claisen condensation, or 1,5-dicarbonyls, which are commonly made using a Michael reaction, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the Paal–Knorr synthesis of furans and pyrroles. Traditionally utilized catalysts for the Stetter reaction are thiazolium salts and cyanide anion, but more recent work toward the asymmetric Stetter reaction has found triazolium salts to be effective. The Stetter reaction is an example of umpolung chemistry, as the inherent polarity of the aldehyde is reversed by the addition of the catalyst to the aldehyde, rendering the carbon center nucleophilic rather than electrophilic.
Scheme 1. Stetter reaction overview
^Stetter, H. Angew. Chem. Int. Ed.1976, 15, 639.
^Stetter, H. and Schreckenberg, M. Angew. Chem. Int. Ed. Engl.1973, 12, 81.
The Stetterreaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst...
Stetter is a German surname. Notable people with the surname include: Florian Stetter (born 1977), German actor Georg Stetter (1895–1988), Austrian-German...
nitrogen forms a thiazolium cation. Thiazolium salts are catalysts in the Stetterreaction and the Benzoin condensation. Deprotonation of N-alkyl thiazolium salts...
used in the Baylis-Hillman reaction. Thiazolium salts are employed in the Stetterreaction. These catalysts and reactions have a long history but current...
originally isolated from heated sediments in Vulcano, Italy by Fiala and Stetter. It is noted for its rapid doubling time of 37 minutes under optimal conditions...
P. Guilford Richard J. Haier Richard Herrnstein Ronald K. Hoeflin Leta Stetter Hollingworth Lloyd Humphreys Earl B. Hunt Seymour Itzkoff Douglas N. Jackson...
geothermal springs in New Zealand. Nature communications, 9(1), p.2876. Stetter, K. (2006). "History of discovery of the first hyperthermophiles". Extremophiles...
the belief they would be incapable of working for 1 week a month. Leta Stetter Hollingworth wanted to prove this hypothesis and Edward L. Thorndike's...
doi:10.1098/rstb.2006.1881. ISSN 0962-8436. PMC 2442388. PMID 17255002. Stetter, Karl O (29 October 2006). "Hyperthermophiles in the history of life"....
Harald; Hohn, Michael J.; Rachel, Reinhard; Fuchs, Tanja; Wimmer, Verena C.; Stetter, Karl O. (May 2002). "A new phylum of Archaea represented by a nanosized...
Geiger, Otto Hahn, Paul Harteck, Gerhard Hoffmann, Josef Mattauch and Georg Stetter. A second meeting was held soon thereafter and included Heisenberg, Klaus...
from the original on 21 July 2011. Retrieved 21 October 2010. "SCHWING Stetter Launches New Truck mounted Concrete Pump S-36". NBM&CW (New Building Materials...
1086/716560. hdl:10419/171064. ISSN 0022-3808. S2CID 240811706. Diez, Thomas; Stetter, Stephan; Albert, Mathias (July 2006). "The European Union and Border Conflicts:...
Bibcode:1978JMolE..11....1M. doi:10.1007/bf01768019. PMID 660662. S2CID 1291732. Stetter KO (1996). "Hyperthermophiles in the history of life". Ciba Foundation...
Eastern Europe as a national revival movement in the late 19th century, in reaction to newer waves of antisemitism and as a consequence of the Haskalah, or...
Psychrophile Thermophile Unique properties of hyperthermophilic archaea Stetter, K. (2006). "History of discovery of the first hyperthermophiles". Extremophiles...
is a rapid fast punch that is very difficult to block, based on human reaction time—"the idea is to finish the execution of the punch before the opponent...
Stetter, Karl O. (2011). "Part 4: Extremophiles: Thermophiles". In Koki Horikoshi; Garabed Antranikian; Alan T. Bull; Frank T. Robb; Karl O. Stetter (eds...
PMID 16030242. Blochl E, Rachel R, Burggraf S, Hafenbradl D, Jannasch HW, Stetter KO (1997). "Pyrolobus fumarii, gen. and sp. nov., represents a novel group...
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