Atroposelective Synthesis of 3,3'-Bisindoles Bearing Axial and Central Chirality:Using Isatin-Derived Imines as Electrophiles  

作　　者：Feng-Tao Sheng Zhi-Min Li Yi-Zhu Zhang Li-Xing Sun Yu-Chen Zhang Wei Tan Feng Shi 

机构地区：[1]School of Chemistry and Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116,China

出　　处：《Chinese Journal of Chemistry》2020年第6期583-589,共7页中国化学（英文版）

基　　金：financial support from NSFC(Nos.21772069 and 21831007);Six Kinds of Talents Project of Jiangsu Province(SWYY-025).

摘　　要：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.

关 键 词：INDOLE chiral AXIAL 

分 类 号：O62[理学—有机化学]