Stereoselective formal alkenylation of β,β-disubstituted enesulfinamides for constructing 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic α-quaternary stereocenters

Abstract

Geometry-defined β,β-disubstituted enesulfinamides undergo one-pot conjugate addition–elimination cascade to afford α-alkenylated ketimines with high stereocontrol. By tuning the substituents on Michael acceptors, formal alkenylation transformation allows regiodivergent construction of 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic quaternary α-stereocenters substituted with two sterically and electronically similar groups (e.g., methyl and ethyl).