New strategies for asymmetric photocatalysis: asymmetric organocatalytic/photoredox relay catalysis for efficient synthesis of polycyclic compounds containing vicinal amino alcohols  

作　　者：Jia-Lu Zhang Wen-Bo He Xiu-Qin Hu Peng-Fei Xu 

机构地区：[1]State Key Laboratory of Applied Organic Chemistry,College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,China [2]State Key Laboratory of Veterinary Etiological Biology,College of Veterinary Medicine,Lanzhou University,Lanzhou Veterinary Research Institute,Chinese Academy of Agricultural Sciences,Lanzhou 730000,China [3]MOE Frontiers Science Center for Rare Isotopes,Lanzhou University,Lanzhou 730000,China

出　　处：《Science China Chemistry》2024年第3期945-952,共8页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(21632003,21871116,22071085,U22A20390);the Fundamental Research Funds for the Central Universities(lzujbky-2023-stlt01);the 111 Program from the Ministry of Education of China。

摘　　要：An asymmetric catalytic strategy in photocatalysis utilizing a chirality-induced approach through an organocatalytic/photoredox relay catalysis strategy is successfully achieved for the rapid construction of polycyclic compounds containing vicinal amino alcohols in a one-pot protocol. This methodology facilitates the efficient synthesis of diverse substituted polycyclic tetrahydroquinoline and benzofuran-derived vicinal amino alcohols, each containing five consecutive chiral centers, with high yields,excellent diastereoselectivities and enantioselectivities(up to 95% yield, >20:1 dr and 98% ee), under mild reaction conditions driven by sequential bifunctional squaramide organocatalyst-catalyzed [4+2] annulation and photocatalyst-catalyzed ketyl radical addition cyclization reaction process. Furthermore, investigations into the stereoselectivity mechanism and high-resolution mass spectrometry(HRMS) experiments on free radical trapping have provided evidence for elucidating the detailed mechanism of chirality-induced processes and chiral intermediate conversions in this procedure.

关 键 词：enantioselective photocatalysis asymmetric organocatalytic/photocatalysis relay catalysis five consecutive chiral centers chirality-induced strategy chirality vicinal amino alcohols 

分 类 号：O624.6[理学—有机化学] O643.36[理学—化学] O644.1