Asymmetric synthesis of binaphthyls through photocatalytic crosscoupling and organocatalytic kinetic resolution  

作　　者：Heng-Hui Li Jia-Yan Zhang Shaoyu Li Yong-Bin Wang Jun Kee Cheng Shao-Hua Xiang Bin Tan 

机构地区：[1]School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China [2]Shenzhen Grubbs Institute,Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China [3]Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,518055,China

出　　处：《Science China Chemistry》2022年第6期1142-1148,共7页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China (21825105);the Guangdong Provincial Key Laboratory of Catalysis (2020B121201002);the Guangdong Innovative Program (2019BT02Y335);the Shenzhen Special Funds (JCYJ20190812-112603598, JCYJ20210324120205016);the Shenzhen Nobel Prize Scientists Laboratory Project (C17213101);the SUSTech Special Fund for the Construction of High-Level Universities (G02216302)。

摘　　要：By capitalizing on the capability of photoredox catalysis to generate reactive radical intermediate under mild conditions, we established a photocatalytic cross-coupling protocol that could deliver both derivatives from 1-bromo-2-naphthols in combination with 2-naphthols or 2-naphthylamines. This distinct activation mode could overcome structural or electronic limitation associated with conventional coupling pathways. Additionally, a novel kinetic resolution protocol of unprotected BINOLs has been established with azodicarboxylates via chiral phosphoric acid(CPA) catalysis. Selectivity factor of up to 175 could be achieved and delivered to both enantiomers in atropisomerically enriched form after a simple work-up.

关 键 词：1 1′-bi-2-naphthols 2-amino-2′-hydroxy-1 1′-binaphthyls chiral phosphoric acid kinetic resolution PHOTOCATALYSIS 

分 类 号：TQ241.33[化学工程—有机化工] O643.36[理学—物理化学]