Oxidative asymmetric umpolung alkylation of Evans’ β-keto imides by dialkylzinc nucleophiles

Tom Targel, Chemistry, Technion, Haifa, Israel

An asymmetric application of the hypervalent iodine mediated alkylation of ketones with dialkylzinc is presented. This work relies on the asymmetric induction of the Evans’ auxiliary in the alkylation of β-ketoimides. The reaction affords the products, with diastereomeric ratios ranging between 3:1 to 18:1, and yields of isolated pure single diastereomers ranging between 40% and 80%. This reaction is tolerant of a variety of functional groups and is carried out under mild conditions.