Catalytic Asymmetric Synthesis of Inherently Chiral Saddle- Shaped Dibenzo[b,fI[1,5]diazocines  

作　　者：Jinmiao Zhou Mengyao Tang Xiaoyu Yang 

机构地区：[1]Schoolof Physical Science and Technology,ShanghaiTech University,Shanghai 201210,China

出　　处：《Chinese Journal of Chemistry》2024年第17期1953-1959,共7页中国化学（英文版）

基　　金：The authors gratefully acknowledge NSFC(grant nos.22222107,22171186);China Postdoctoral Science Foundation(2023M742365);Postdoctoral Fellowship Program of CPSF(GZC20231671);ShanghaiTech University start-up funding for financial support.Prof.Guangxin Liang was acknowledged for sharing the optical rotation polarimeter,and Mr.Huanchao Gu was acknowledged for the assistance with X-ray crystallographic analysis;support from Analytical Instrumentation Center(#SPST-AIC10112914),SPST,ShanghaiTech University.

摘　　要：Dibenzo[b,fi[1,5]diazocines are a class of eight-membered heterocycles,which exhibit unique rigid saddle-shaped structure and possess inherent chirality.In this study,we report a convenient and straightforward method for the catalytic enantioselective synthesis of these unique chiral molecules through chiral phosphoric acid-catalyzed dimerization of 2-acylbenzoisocyanates.Notably,the addition of corresponding 2-acylaniline as the co-catalyst significantly improved the efficiency of these reactions,and a simple phase separation operation resulted in products with excellent enantiopurity.Experimental studies were performed to elucidate the mechanism behind these reactions,leading to the proposal of a plausible reaction mechanism based on the study findings.

关 键 词：Dibenzo[b f][1 5]diazocines Saddle-shaped inherent chirality ORGANOCATALYSIS Asymmetric catalysis Medium-ring compounds Cooperativecatalysis Chiral phosphoricacids 

分 类 号：O62[理学—有机化学]