Fuentes de Arriba Angel L, Urbitsch Felix, Dixon Darren J
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK.
Chem Commun (Camb). 2016 Dec 13;52(100):14434-14437. doi: 10.1039/c6cc09172e.
A three component reductive coupling reaction of a (hetero)aromatic amine, a (hetero)aromatic aldehyde and an electron deficient olefin catalysed by eosin Y under green LED light irradiation, for the direct generation of γ-amino acid derivatives, is described. This new umpolung synthesis of amines, which exploits the high nucleophilicity of a putative α-amino radical intermediate, generated via single electron reduction of the in situ generated imine from the Hantzsch ester terminal reductant, is efficient, operationally simple, broad in scope and offers a complementary strategy to existing synthetic approaches.
描述了在绿色LED光照射下，由曙红Y催化的（杂）芳族胺、（杂）芳族醛和缺电子烯烃的三组分还原偶联反应，用于直接生成γ-氨基酸衍生物。这种新的胺的极性反转合成方法利用了假定的α-氨基自由基中间体的高亲核性，该中间体是通过从汉茨酯末端还原剂原位生成的亚胺的单电子还原产生的，具有高效、操作简单、适用范围广的特点，并为现有的合成方法提供了一种补充策略。
