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2005
Ketones
Q 0350
33- 092
Direct Conversion of N-Methoxy-N-methylamides (Weinreb Amides) to Ketones
via a Nonclassical Wittig Reaction. — A new transformation permits the efficient
synthesis of ketones via reaction of Weinreb amide substrates with various alkylidene
triphenylphosphoranes and in situ hydrolysis of the intermediate products. The conditions are much milder than in the conventional route using organometallic reagents. The
reaction is applicable to a large variety of amides including aromatic and aliphatic ones
(chained and branched). Attempts to convert the amide (VIa) of pivalic acid are not
successful. An intramolecular version is also presented [cf. (XVI)]. — (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. 7 (2005) 7, 1427-1429; Dep.
Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK; Eng.) — R. Steudel
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