Enantioselective Nucleophilic Vinylic Substitution (SNV) toward 3-Alkenyl-bisoxindoles Facilitated by C6 & PRIME; Steric Bulk of Cinchona Alkaloid

A C6 & PRIME; bulky substituted quinine-catalyzed S(N)Vreaction between 3-substituted oxindole and (E)-3-(nitromethylene)-oxindolewas developed. This enantioselective C(sp (3))-C(sp (2)) coupling furnished bisoxindolescaffolds featuring a vinyl-substituted all-carbon quaternary stereocenterwith high stereoselectivities. In addition, the gram-scale synthesisand synthetic post-transformations were conducted to demonstrate thepotential synthetic usefulness.