Stereoselective Construction of Acyclic β,β-Disubstituted Enesulfinamides via Conjugate Addition of Organocuprates to α-Substituted α,β-Unsaturated N-Sulfinyl Ketimines.

Abstract

In the presence of boron trifluoride, conjugate addition of organocuprates to α-substituted α,β-unsaturated N-tert-butanesulfinyl ketimines provides facile access to acyclic β,β-disubstituted enesulfinamides with high ratios of geometric isomers. Diverse and challenging to synthesize, multisubstituted aza-enolates bearing two electronically and sterically similar β-substituents, which are important precursors for asymmetric construction of the less accessible acyclic quaternary or tetrasubstituted stereocenters at the α-position of ketimines, can be efficiently prepared in good yields with high stereocontrol.