Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines

• DOI: 10.1021/acs.orglett.4c01003
• Publication Date: 2024-04-08T12:25:10Z
• Authors: Pei-Hao Dou; Xiao-Hui Fu; Yan Chen; Zhen-Zhen Ge; Ming-Qiang Zhou; Zhen-Hua Wang; Yong You; Lei Yang; Yan-Ping Zhang; Jian-Qiang Zhao; Wei-Cheng Yuan
• Keywords: Stereocenter; Decarboxylation; Phosphoramidite; Amide

A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable triggering dearomatization 3-nitroindoles for diastereo- enantioselective [3+2] cycloaddition, leading formation series highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up 99% yield, 88:12 dr, 96% ee).