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Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)‐Catalyzed C−H Activation/Carbene Insertion/Lossen Rearrangement Sequence
Author(s) -
Ma Biao,
Wu Peng,
Wang Xing,
Wang Zhengyu,
Lin HaiXia,
Dai HuiXiong
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201906589
Subject(s) - carbene , chemistry , annulation , rhodium , catalysis , cascade reaction , diazo , combinatorial chemistry , insertion reaction , nucleophile , stereochemistry , medicinal chemistry , organic chemistry
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.