Title Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence
Authors Ma, Biao
Wu, Peng
Wang, Xing
Wang, Zhengyu
Lin, Hai-Xia
Dai, Hui-Xiong
Affiliation Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China
Peking Univ, Stake Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
Keywords C-H activation
Lossen rearrangement
olefins
oxindoles
rhodium catalysis
Issue Date 2019
Publisher ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Abstract A rhodium(III)-catalyzed domino annulation of simple olefins with diazo oxindoles to give spirooxindole pyrrolone products is described. This reaction can be formally viewed as the result of an anomalous tandem C-H activation, carbene insertion, Lossen rearrangement, and a nucleophilic addition process. The potential utility of this reaction was further demonstrated by the late-stage diversification of drug molecules.
URI http://hdl.handle.net/20.500.11897/545964
ISSN 1433-7851
DOI 10.1002/anie.201906589
Indexed SCI(E)
EI
Appears in Collections: 天然药物与仿生药物国家重点实验室

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