Weinreb ketone synthesis
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The Weinreb ketone synthesis is a chemical reaction used to transform N,O-dimethylhydroxamic acids (Weinreb amides, 1) into ketones (3).
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 ylides.
Weinreb amides are synthesized typically from their corresponding carboxylic acids.
[edit] Variations
Reaction of Weinreb amides with lithium aluminium hydride will form aldehydes.
[edit] 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). (Article)
