Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

Abstract

An efficient Rh^II -catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C-C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

Keywords: carbene chemistry; enaminones; ruthenium; synthetic methods; α-vinyl aldehydes.