Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2-<i>a</i>]indoles via Dynamic Kinetic Resolution of Allene Intermediates
作者:Jian-Fei Bai、Lulu Zhao、Fang Wang、Fachao Yan、Taichi Kano、Keiji Maruoka、Yuehui Li
DOI:10.1021/acs.orglett.0c01812
日期:2020.7.17
straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93% yield and 98% ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.
我们报道了手性磷酸催化的3-取代的1 H-吲哚和含有功能性导向基团(对-NHAc或对-OH)的炔丙醇的正式(3 + 2)环加成反应。这项工作代表了一种简单的方法来合成带有四取代碳立体中心的手性吡咯并[1,2- a ]吲哚。反应以多种底物耐受性顺利进行,以高达93%的收率和98%ee的产率递送各种手性吡咯并[1,2- a ]吲哚。通过将产物多样化转化为各种吲哚衍生物,突出了该方法的实用性。