Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
J Org Chem. 2020 Nov 6;85(21):13920-13928. doi: 10.1021/acs.joc.0c01974. Epub 2020 Oct 9.
A blue light-promoted formal [4+1]-annulation of diazoacetates with -aminoacetophenones has been reported, which provides an environmentally friendly method for the synthesis of polysubstituted indoline derivatives in moderate to good yields with excellent diastereoselectivities. Detailed mechanistic studies through density functional theory calculations reveal that the ()-enol species is the key intermediate in this transformation, and the excellent diastereoselectivity is enabled -bonding in the intramolecular Aldol-type addition.
报道了一种蓝光促进的重氮乙酸酯与 - 氨基苯乙酮的[4+1]-环化反应，为多取代吲哚啉衍生物的合成提供了一种环境友好的方法，产率中等至良好，具有优异的非对映选择性。通过密度泛函理论计算的详细机理研究表明，（）-烯醇物种是该转化中的关键中间体，并且优异的非对映选择性是通过分子内Aldol 型加成中的 - 键实现的。
