Enantioselective Nucleophilic Vinylic Substitution (S<sub>N</sub>V) toward 3-Alkenyl-bisoxindoles Facilitated by C6′ Steric Bulk of Cinchona Alkaloid
Xingyue Wang, Guishun Bai, Ruoqi Liu, Xiao-Li Zhu, Xinyi Ye, Tao Zhang, Kui Zhang, Damien Bonne, Jean Rodriguez, Hong Wang, Xiaoze Bao
Abstract
A C6′ bulky substituted quinine-catalyzed S N V reaction between 3-substituted oxindole and ( E )-3-(nitromethylene)-oxindole was developed. This enantioselective C( sp 3 )–C( sp 2 ) coupling furnished bisoxindole scaffolds featuring a vinyl-substituted all-carbon quaternary stereocenter with high stereoselectivities. In addition, the gram-scale synthesis and synthetic post-transformations were conducted to demonstrate the potential synthetic usefulness.
Topics & Concepts
ChemistryCinchonaOxindoleStereocenterEnantioselective synthesisSteric effectsAlkaloidStereochemistryOrganic chemistryCombinatorial chemistryCatalysisAsymmetric Synthesis and CatalysisOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods