Alkylation of Ethyl Pyruvate via Reductive Coupling of Alkenes and Ethyl 2-(Benzenesulfonylamino)acrylate

Abstract

Radical coupling of B-alkylcatecholboranes, in situ generated from the corresponding alkenes, with ethyl 2-(benzenesulfonylamino)acrylate is reported. This reaction represents an extension of the radical allylation of Balkylcatecholboranes by allylsulfones. This unique process allows the preparation of various ?-ketoesters (alkylated pyruvates) in a straightforward manner. It also demonstrates the generality of the radical mediated C–C bond formation starting from organoboranes and allylic benzenesulfonyl derivatives.

Keywords

• Alkylation
• Enamides
• Hydroboration
• Organoboranes
• Radical reactions
• Sulfonamides