4.7 Article

Catalyzed reactions of enol ethers with SN1 active groups:: A novel method for the preparation of α-alkylated ketones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 345, Issue 8, Pages 1017-1030

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200303059

Keywords

alkylation; boron; catalysis; copper; enolates; Lewis acids; ketones

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The performance of tert-alkylations, alkoxyalkylations, and aldehyde enolate allylations proceeding with low catalyst loading (0.1mol % -5mol%) is described. The reactions are complete within short times and can even be performed without solvent and under ambient conditions. The mechanism of the reaction was investigated by deuterium labeling and cross-over studies.

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