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Photocatalyzed Intramolecular [2+2] Cycloaddition of N‐Alkyl‐N‐(2‐(1‐arylvinyl)aryl)cinnamamides
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2020-09-21 , DOI: 10.1002/chem.202003641
Wanderson C de Souza 1 , Bianca T Matsuo 1 , Priscilla M Matos 1 , José Tiago M Correia 1 , Marilia S Santos 1, 2 , Burkhard König 2 , Marcio W Paixão 1
Affiliation  

N‐Alkyl‐N‐(2‐(1‐arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin‐3(1H)‐ones, in yields ranging between 20–99 %, and with excellent regio‐ and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]‐cycloaddition of 1,7‐enynes—after fragmentation of the cyclobutane ring—leads to enyne‐metathesis‐like products.

中文翻译:

N-烷基-N-(2-(1-(芳基乙烯基)芳基)肉桂酰胺的光催化分子内[2 + 2]环加成反应

N-烷基-N-( 2-(1-芳基乙烯基)芳基)肉桂酰胺通过铱光催化的分子内[2 + 2]光环加成反应转变为天然产物。该协议具有广泛的底物范围,同时在温和的反应条件下运行。束缚形成三取代的环丁烷核心的四个成分会迅速建立高分子复杂性。我们的方法允许设计和合成多种四氢环丁酮[ c ]喹啉-3(1 H)-酮,产率在20–99%之间,并且具有出色的区域选择性和非对映选择性。此外,已证明在环丁烷环断裂后,1,7-烯炔的分子内[2 + 2]-环加成反应会导致类似烯炔的复分解。
更新日期:2020-09-21
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