Gold‐Catalyzed Cycloaddition Reactions of Ethyl Diazoacetate,Nitrosoarenes, and Vinyldiazo Carbonyl Compounds: Synthesis of Isoxazolidine and Benzo[b]azepine Derivatives |
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| Authors: | Dr. Vinayak Vishnu Pagar Prof. Dr. Rai‐Shung Liu |
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| Affiliation: | Department of Chemistry, National Tsing‐Hua University, Hsinchu, 30043, Taiwan (ROC) |
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| Abstract: | 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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| Keywords: | cycloaddition diazo compounds gold heterocycles synthetic methods |
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