Weinreb ketone synthesis

Weinreb ketone synthesis

The Weinreb ketone synthesis is a chemical reaction used to transform N,O-dimethylhydroxamic acids (Weinreb amides, 1) into ketones (3).Ref|Weinreb1981

Addition of the organometallic nucleophile to the Weinreb amide produces a stable tetrahedral chelate (2), which upon hydrolysis produces the desired ketone.

Applicable organometallic nucleophiles include organolithium reagents, Grignard reagents, and phosphonium ylidesRef|Murphy2005.

Weinreb amides are synthesized typically from their corresponding carboxylic acids.Ref|Fehrentz1983Ref|DeLuca2001Ref|Woo2004Ref|Tunoori2000

Variations

Reaction of Weinreb amides with lithium aluminium hydride will form aldehydes.Ref|Goel1989

References

# Nahm, S.; Steve M. Weinreb "Tetrahedron Lett." 1981, "22", 3815-3818.
# Murphy, J. A.; Commeureuc, A. G. J.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. "Org. Lett." 2005, "7", 1427-1429. DOI|10.1021/ol050337b
# Fehrentz, J.-A.; Castro, B. "Synthesis" 1983, 676.
# De Luca, L.; Giacomelli, G.; Taddei, M. "J. Org. Chem." 2001, "66", 2535-2537.
# Woo, J. C. S.; Fenster, E.; Dake, G. R. "J. Org. Chem." 2004, "69", 8984-8986.
# Tunoori, A. R.; White, J. M.; Georg, G. I. "Org. Lett." 2000, "2", 4091-4093.
# Goel, O. P.; Krolls, U.; Stier, M.; Kesten, S. "Organic Syntheses", Coll. Vol. 8, p.68 (1993); Vol. 67, p.69 (1989). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv8p0068 Article] )

ee also

* Reformatsky reaction
* "weinreb amide" is mentioned near the bottom of the image in the section Crimmins_thiazoldinethione_aldol of the article Aldol_reaction


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