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Gold-catalyzed cycloaddition reactions of ethyl diazoacetate, nitrosoarenes, and vinyldiazo carbonyl compounds: Synthesis of isoxazolidine and benzo[b]azepine derivatives
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Gold-catalyzed cycloaddition reactions of ethyl diazoacetate, nitrosoarenes, and vinyldiazo carbonyl compounds: Synthesis of isoxazolidine and benzo[b]azepine derivatives

Vinayak Vishnu PagarRai-Shung Liu
Angewandte Chemie - International Edition, 卷.54(16), 頁碼.4923-4926
04/2015

摘要

cycloaddition diazo compounds gold heterocycles synthetic methods Catalysis Chemistry (all)
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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