Enantioselective Diels-Alder reactions with left-handed G-quadruplex DNA-based catalysts  

作　　者：Kun Chen Zhiyong He Wei Xiong Chun-Jiang Wang Xiang Zhou 

机构地区：[1]College of Chemistry and Molecular Sciences,Key Laboratory of Biomedical Polymers of Ministry of Education,Wuhan University,Wuhan 430072,China

出　　处：《Chinese Chemical Letters》2021年第5期1701-1704,共4页中国化学快报（英文版）

基　　金：This work was supported by the National Natural Science Foundation of China(Nos.21432008,91753201,and 21721005).

摘　　要：Since the discovery of left-handed G-quadruplex(L-G4)structure formed by natural DNA,there has been a growing interest in its potential functions.This study utilised it to catalyse enantioselective Diels-Alder reactions,considering its different optical rotation compared to an ordinary G4.It was determined that when L-G4 was used with a combination of copper(Ⅱ)ions,there was a good enantioselectivity(-52%ee)without further addition of ligands.When further consideration was given by adding G4 ligands,G4 was further stabilised,even obtaining a better enantioselectivity(up to-80%ee).Moreover,when using ligands that have regulatory effects on G4,the ee value can be adjusted.In this work,a minimal left-handed G4 was reported.A follow-up study was also con ducted,which recovers that the minimal left-handed G4 remains its catalytic effect and enantioselectivity,but is not so effective as the former case.This indicates that a complete G4 structure is relatively conducive to chiral catalysis.

关 键 词：Diels-Alder reaction Left-handed G-quadruplex Asymmetric catalysis Enantioselectiv ity G-quadruplex ligand 

分 类 号：O621.251[理学—有机化学]