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Gold‐Catalyzed Cycloaddition Reactions of Ethyl Diazoacetate, Nitrosoarenes, and Vinyldiazo Carbonyl Compounds: Synthesis of Isoxazolidine and Benzo[ b ]azepine Derivatives
Author(s) -
Pagar Vinayak Vishnu,
Liu RaiShung
Publication year - 2015
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.201500340
Subject(s) - azepine , ethyl diazoacetate , cycloaddition , chemistry , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , cyclopropanation
Gold‐catalyzed cycloadditions of ethyl diazoacetate, nitrosoarenes, and vinyldiazo carbonyl species to yield isoxazolidine derivatives stereoselectively are described. Treatment of these isoxazolidine products with the same catalyst results in a novel 1,2‐H shift/[3,3] rearrangement to give benzo[b]azepine compounds. The mechanism of this skeletal rearrangement is elucidated with deuterium‐labeling experiments.