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

文献类型： 外文期刊

第一作者： Zhang, Jia-Lu

作者： Zhang, Jia-Lu;He, Wen-Bo;Hu, Xiu-Qin;Xu, Peng-Fei;Xu, Peng-Fei;Xu, Peng-Fei

作者机构：

关键词： enantioselective photocatalysis; asymmetric organocatalytic/photocatalysis relay catalysis; five consecutive chiral centers; chirality-induced strategy; chirality vicinal amino alcohols

期刊名称：SCIENCE CHINA-CHEMISTRY （ 影响因子：9.6； 五年影响因子：7.2 ）

ISSN： 1674-7291

年卷期： 2024 年 67 卷 3 期

页码：

收录情况： SCI

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 tetra-hydroquinoline 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.

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