Regioselective α-Alkylation of Ketones via Magnesium Enamides

Significance

Alkylation of ketones via their metal enolates is one of the fundamental C-C bond-forming reactions in organic chemistry. However, the scope and selectivity of this process is often not satisfactory. The authors report herein a great improvement of this reaction, allowing to use usually unreactive primary and secondary alkyl chlorides and fluorides as electrophiles, with excellent regio- and often good stereoselectivity. Use of enantiopure benzyl halides afforded products with good enantioselectivities.