Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 16, Pages 4923-4926Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500340
Keywords
cycloaddition; diazo compounds; gold; heterocycles; synthetic methods
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Funding
- Ministry of Science and Technology, Taiwan
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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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