Alkylation of Highly Stabilized Enolates

Akimoto, K. Aoki, M. Shindo, and K. Koga, Chem. Pharm. Bull., 48, 1529 (2000). 

47 For general reviews of enolate alkylation, see D. Caine, in Carbon-Carbon Bond Formation, Vol. 1, R. L. Augustine, ed., Marcel Dekker, New York, 1979, Chap. 2 C. H. Heathcock, Modem Synthetic Methods, 6, 1 (1992). 

P-keto acid X = alkyl or aryl = ketone substituted malonic acid X=OH = substituted acetic acid 

In the preparation of 2-heptanone (Entry 1), for example, ethyl acetoacetate functions 

It is also possible to use the dilithium derivative of acetoacetic acid as the synthetic equivalent of acetone enolate.49 In this case, the hydrolysis step is unnecessary and decarboxylation can be done directly on the alkylation product. 

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