Lewis Acid Alkylation of Ketones Using SN1-reactive Acetates

Reetz, M. T.; Hüttenhain, S.; Hübner, F.

doi:10.1080/00397918108061863

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Lewis Acid Alkylation of Ketones Using S_N1-reactive Acetates

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Reetz, M. T., Hüttenhain, S., & Hübner, F. (1981). Lewis Acid Alkylation of Ketones Using S_N1-reactive Acetates. Synthetic Communications, 11(3), 217-222. doi:10.1080/00397918108061863.

Cite as: https://hdl.handle.net/21.11116/0000-000E-A397-F

Abstract

The reaction of carbonic acid esters RCO₂R¹ with carbanions R²−Metal such as Grignard reagents or enolate anions fails to produce R¹−R² encounters due to preferred attack at the carbonyl function¹. We have now discovered that S_N1-reactive acetic acid esters undergo smooth C-C-bond formation with silyl enol ethers² in the presence of ZnI₂ to afford α-alkylated ketones. Products due to Claisen ester condensation are not observed. As a prime example, 1 or 2 were found to be excellent prenylating agents.