Lewis Acid Induced α‐Alkylation of Carbonyl Compounds

Carbonyl compounds undergo α‐alkylation via the corresponding silyl enol ethers using S N 1 active alkyl halides or acetates in the presence of Lewis acids. This methodology extends the scope of carbonyl chemistry considerably, since S N 1 active alkylating agents are generally base sensitive and therefore unsuitable for reactions with enolate anions or nitrogen analogs. A prime example is the α‐ tert ‐alkylation of aldehydes, ketones and esters.