Lewis Acid Alkylation of Ketones Using SN1-reactive Acetates
MT Reetz, S Hüttenhain, F Hübner
Index: Reetz, M. T.; Huettenhain, S.; Huebner, F. Synthetic Communications, 1981 , vol. 11, # 3 p. 217 - 222
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Citation Number: 16
Abstract
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 SN1-reactive acetic acid esters undergo smooth CC-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. ...
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