Enantioselective Radical‐Polar Crossover Reactions of Indanonecarboxamides with Alkenes

作者：Xiying Zhang, Wangbin Wu, Weidi Cao, Yu Han, Xi Xu, Xiaohua Liu, Xiaoming Feng · 发表于：Angewandte Chemie International Edition · 年份：2020 · DOI：10.1002/anie.201914151 · 被引用次数：35 · 研究领域：Catalytic C–H Functionalization Methods、Radical Photochemical Reactions、Oxidative Organic Chemistry Reactions

Abstract Highly efficient asymmetric intermolecular radical‐polar crossover reactions were realized by combining a chiral N , N ′‐dioxide/Ni II complex catalyst with Ag 2 O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro‐iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee ). Furthermore, a range of different radical‐mediated oxidation/elimination or epoxide ring‐opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.