Photocatalytic reverse polarity Povarov reaction†,Chemical Science

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Photocatalytic reverse polarity Povarov reaction†
Chemical Science ( IF 7.6 ) Pub Date : 2018-07-06 00:00:00 , DOI: 10.1039/c8sc01704b
Jamie A Leitch ₁ , Angel L Fuentes de Arriba ₁ , Joanne Tan ₂ , Oskar Hoff ₁ , Carlos M Martínez ₃ , Darren J Dixon ₁

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A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating via a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the trans diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.

中文翻译：

光催化反极性波瓦罗夫反应†

描述了芳基亚胺和缺电子烯烃的可见光介导的铱光催化反极性波瓦罗夫反应。通过质子偶联电子转移过程产生的推定的亲核 α-氨基自由基，添加到一系列共轭缺电子烯烃底物中，可以高产率提供取代的四氢喹啉产物，并且通常具有良好至优异的非对映选择性，有利于反式非对映异构体。亚化学计量的 Hantzsch 酯被发现是引发整个氧化还原中性自由基环化级联的关键。这种新反应补充了现有的两种电子路易斯酸介导的变体，并将亚胺反极化化学的能力扩展到合成相关的环化方法。

更新日期：2018-07-06

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