对映选择合成
发色团
化学
催化作用
布朗斯特德-洛瑞酸碱理论
路易斯酸
分子间力
背景(考古学)
激发态
光化学
立体化学
组合化学
有机化学
分子
古生物学
物理
生物
核物理学
作者
Evan M. Sherbrook,Matthew J. Genzink,Bohyun Park,Ilia A. Guzei,Mu‐Hyun Baik,Tehshik P. Yoon
标识
DOI:10.1038/s41467-021-25878-9
摘要
Control over the stereochemistry of excited-state photoreactions remains a significant challenge in organic synthesis. Recently, it has become recognized that the photophysical properties of simple organic substrates can be altered upon coordination to Lewis acid catalysts, and that these changes can be exploited in the design of highly enantioselective catalytic photoreactions. Chromophore activation strategies, wherein simple organic substrates are activated towards photoexcitation upon binding to a Lewis acid catalyst, rank among the most successful asymmetric photoreactions. Herein, we show that chiral Brønsted acids can also catalyze asymmetric excited-state photoreactions by chromophore activation. This principle is demonstrated in the context of a highly enantio- and diastereoselective [2+2] photocycloaddition catalyzed by a chiral phosphoramide organocatalyst. Notably, the cyclobutane products arising from this method feature a trans-cis stereochemistry that is complementary to other enantioselective catalytic [2+2] photocycloadditions reported to date.
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