A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization

Facile access to enantioenriched isoindolines bearing a quaternary stereogenic center and a tertiary stereogenic center was successfully developed via highly efficient Cu(I)/(S,Rp)-PPFOMe-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylide with quinone derivatives followed by silica-gel-promoted aromatization in a one-pot reaction protocol. The present catalytic system exhibited high diastereoselectivity, excellent enantioselectivity, and a broad substrate scope under mild conditions.

本研究成功建立了简便的制备方法，可得到同时含有手性季碳中心与手性叔碳中心的对映体富集的异吲哚啉（isoindolines）类化合物。该方法以高效铜(I)/(S,Rp)-PPFOMe催化的甲亚胺叶立德（azomethine ylide）与醌类衍生物（quinone derivatives）的不对称1,3-偶极环加成（1,3-dipolar cycloaddition）反应为核心，结合硅胶促进的芳构化（silica-gel-promoted aromatization）过程，采用一锅法反应策略完成整体转化。所采用的催化体系在温和反应条件下，展现出优异的非对映选择性、出色的对映选择性以及宽泛的底物适用范围。