Visible Light-Mediated Cobalt and Photoredox Dual-Catalyzed Asymmetric Reductive Coupling for Axially Chiral Secondary Alcohols  

作　　者：Tianlong Liang Yingtao Wu Jiaqiong Sun Mingrui Li Huaqiu Zhao Jingjing Zhang Guangfan Zheng Qian Zhang 

机构地区：[1]Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province,Department of Chemistry,Northeast Normal University,Changchun,Jilin,130024 China [2]School of Environment,Northeast Normal University,Changchun,Jilin,130117 China [3]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Road,Shanghai,200032 China

出　　处：《Chinese Journal of Chemistry》2023年第23期3253-3260,共8页中国化学（英文版）

基　　金：Natural Science Foundation of Jilin Province(20230101047JC,YDZJ202201ZYTS338);NSFC(22001157,21831002,22193012,and 22201033);Jilin Educational Committee(JJKH20231295KJ,JJKH20231302KJ);the Fundamental Research Funds for the Central Universities(2412022ZD012,2412022QD016,2412021QD007)for generous financial support.

摘　　要：Secondary alcohols bearing both axial and central chirality comprise attractive biological activity and exhibit excellent chiral induction in asymmetric reactions.However,only very limited asymmetric catalytic approaches were developed for their synthesis.We herein describe visible light-mediated cobalt-catalyzed asymmetric reductive Grignard-type addition of aryl iodides with axially prochiral biaryl dialdehydes leading to the direct construction of axially chiral secondary alcohols.Preliminary mechanistic studies indicate that efficient kinetic recognition of diastereomers might occur for axially prochiral dialdehydes to improve the stereoselectivity,which might open a new avenue for the challenging cascade construction of multiple chiral elements.This protocol features excellent enantio-and diastereoselectivity,green and mild conditions,simple operation,and broad substrate scope,providing a modular platform for the synthesis of secondary axially chiral alcohols.

关 键 词：Photocatalysis Asymmetric catalysis Reductive Grignard-type addition Aldehydes Secondary axially chiral alcohols DESYMMETRIZATION 

分 类 号：O62[理学—有机化学]