Metal-Free Visible Light-Mediated Photocatalysis: Controlling Intramolecular [2+2] Photocycloaddition of Enones through Axial Chirality
Metal-Free Visible Light-Mediated Photocatalysis: Controlling Intramolecular [2+2] Photocycloaddition of Enones through Axial Chirality
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DOI：
10.1021/acs.joc.6b01066
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发表时间：
2016-08-19
影响因子：
3.6
通讯作者：
Sivaguru, Jayaraman
中科院分区：
文献类型：
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作者：
Clay, Anthony;Vallavoju, Nandini;Sivaguru, Jayaraman
对分子内[2+2]光环加成反应中具有N-C-芳基键旋转的异构烯-酮酰亚胺和烯酮-酰胺进行了评价。与交叉加成产物相比，可观察到直接加成产物，反应活性控制良好。阿托品的选择性依赖于芳环上的取代基。基于不同的机制途径，替代依赖的阿托品选择性被合理化。
Atropisomeric enone-imides and enone-amides featuring N-C-Aryl bond rotation were evaluated for intramolecular [2 + 2] photocycloaddition. Straight addition product was observed over cross-addition product with good control over reactivity. The atropselectivity was found to be dependent on the substituent on the aryl ring. Substitution dependent atropselectivity was rationalized on the basis of a divergent mechanistic pathway.