The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area of research due to the unique characteristics of such frameworks.Nevertheless,research in this area is still in its ...The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area of research due to the unique characteristics of such frameworks.Nevertheless,research in this area is still in its infancy and has some challenges,such as designing and constructing new classes of axially chiral indole-based scaffolds and developing their applications in chiral catalysts,ligands,etc.To overcome these challenges,we present herein the design and atroposelective synthesis of aryl-pyrroloindoles as a new class of axially chiral indole-based scaffolds via the strategy of organocatalytic asymmetric(2+3)cyclization between 3-arylindoles and propargylic alcohols.More importantly,this new class of axially chiral scaffolds was derived into phosphines,which served as efficient chiral ligands in palladium-catalyzed asymmetric reactions.Moreover,theoretical calculations provided an in-depth understanding of the reaction mechanism.This work offers a new strategy for constructing axially chiral indole-based scaffolds,which are promising for finding more applications in asymmetric catalysis.展开更多
Chiral seven-membered ring systems such as seven-membered carbocycles and heterocycles are widely found in natural products and pharmaceuticals.Therefore,the catalytic enantioselective construction of such frameworks ...Chiral seven-membered ring systems such as seven-membered carbocycles and heterocycles are widely found in natural products and pharmaceuticals.Therefore,the catalytic enantioselective construction of such frameworks has evoked considerable interest in the field of chemistry.Among the various approaches,organocatalytic asymmetric(4+3)cycloadditions are highly effective for the enantioselective construction of seven-membered rings.Over the past two decades,substantial efforts have been devoted to this field and chemists have developed various organocatalytic asymmetric(4+3)cycloadditions.This review summarizes the progress in organocatalytic asymmetric(4+3)cycloadditions from 2003 to early 2022 and provides insights into challenging issues faced in this research field,enabling the future development of this field.展开更多
基金support from the National Natural Science Foundation of China (22125104 and 21831007)Natural Science Foundation of Jiangsu Province (BK20210916)High Education Natural Science Foundation of Jiangsu Province (21KJB150009).
文摘The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area of research due to the unique characteristics of such frameworks.Nevertheless,research in this area is still in its infancy and has some challenges,such as designing and constructing new classes of axially chiral indole-based scaffolds and developing their applications in chiral catalysts,ligands,etc.To overcome these challenges,we present herein the design and atroposelective synthesis of aryl-pyrroloindoles as a new class of axially chiral indole-based scaffolds via the strategy of organocatalytic asymmetric(2+3)cyclization between 3-arylindoles and propargylic alcohols.More importantly,this new class of axially chiral scaffolds was derived into phosphines,which served as efficient chiral ligands in palladium-catalyzed asymmetric reactions.Moreover,theoretical calculations provided an in-depth understanding of the reaction mechanism.This work offers a new strategy for constructing axially chiral indole-based scaffolds,which are promising for finding more applications in asymmetric catalysis.
基金supported by the National Natural Science Foundation of China(22125104,21831007)the Natural Science Foundation of Jiangsu Province(BK20210916)the High Education Natural Science Foundation of Jiangsu Province(21KJB150009)。
文摘Chiral seven-membered ring systems such as seven-membered carbocycles and heterocycles are widely found in natural products and pharmaceuticals.Therefore,the catalytic enantioselective construction of such frameworks has evoked considerable interest in the field of chemistry.Among the various approaches,organocatalytic asymmetric(4+3)cycloadditions are highly effective for the enantioselective construction of seven-membered rings.Over the past two decades,substantial efforts have been devoted to this field and chemists have developed various organocatalytic asymmetric(4+3)cycloadditions.This review summarizes the progress in organocatalytic asymmetric(4+3)cycloadditions from 2003 to early 2022 and provides insights into challenging issues faced in this research field,enabling the future development of this field.
