Gold‐Catalyzed Cycloaddition Reactions of Ethyl Diazoacetate, Nitrosoarenes, and Vinyldiazo Carbonyl Compounds: Synthesis of Isoxazolidine and Benzo[ b ]azepine Derivatives
2015; Wiley; Volume: 54; Issue: 16 Linguagem: Inglês
10.1002/anie.201500340
ISSN1521-3773
AutoresVinayak Vishnu Pagar, Rai‐Shung Liu,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAbstract 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.
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