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Enantioselective Radical‐Polar Crossover Reactions of Indanonecarboxamides with Alkenes
Author(s) -
Zhang Xiying,
Wu Wangbin,
Cao Weidi,
Yu Han,
Xu Xi,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914151
Subject(s) - chemistry , enantioselective synthesis , epoxide , catalysis , polar , lewis acids and bases , intermolecular force , radical , chiral lewis acid , reaction conditions , medicinal chemistry , organic chemistry , molecule , physics , astronomy
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.