An atroposelective synthesis of a new class of 3,3'-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles(23 e...An atroposelective synthesis of a new class of 3,3'-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles(23 examples,up to 80% yield,>95:5 do 98:2 er).This approach takes advantage of chiral phosphoric acid-catalyzed dynamic kinetic resolution of 2-substituted 3,3'-bisindoles via nucleophilic addition of such substrates with isatin-derived imines.In this approach,isatin-derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size,which provided an easy access to axially chiral 3,3'-bisindoles incorporated with a biologically important chiral 3-aminooxindole unit.This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3'-bisindole derivatives bearing both axial and central chirality.展开更多
基金financial support from NSFC(Nos.21772069 and 21831007)Six Kinds of Talents Project of Jiangsu Province(SWYY-025).
文摘An atroposelective synthesis of a new class of 3,3'-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles(23 examples,up to 80% yield,>95:5 do 98:2 er).This approach takes advantage of chiral phosphoric acid-catalyzed dynamic kinetic resolution of 2-substituted 3,3'-bisindoles via nucleophilic addition of such substrates with isatin-derived imines.In this approach,isatin-derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size,which provided an easy access to axially chiral 3,3'-bisindoles incorporated with a biologically important chiral 3-aminooxindole unit.This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3'-bisindole derivatives bearing both axial and central chirality.
