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[Structure: see text] A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give alpha-monoalkylated esters and thermodynamically unfavorable (less accessible) alpha,alpha-dialkylated beta-keto esters in good yield (46 examples; 41-98% yield). A closely related reaction between ketene silyl thioacetals (KSTAs) and acid chlorides also proceeded smoothly to give alpha-monoalkylated and alpha,alpha-dialkylated beta-keto thioesters (21 examples; 61-97% yield). The present protocol was extended to the direct condensation of KSAs with carboxylic acids (14 examples; 71-97% yield).
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Iida et al. (2006) studied this question.
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