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Copper-Catalyzed Three-Component Annulations of Alkenes, Nitrosoarenes, and N-Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles
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Copper-Catalyzed Three-Component Annulations of Alkenes, Nitrosoarenes, and N-Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles

Rahul Kisan KawadeRai-Shung Liu
Angewandte Chemie - International Edition, 卷.56(8), 頁碼.2035-2039
2017

摘要

amino alcohols annulations copper catalysis dipolar [3+2]-cycloadditions heterocycles Catalysis Chemistry (all)
One-pot cascade annulations among nitrosoarenes, alkenes, and N-hydroxyallylamines have been achieved with CuCl/O <sub>2</sub> catalysts, forming fused oxazinane/isoxazolidine heterocycles with excellent diastereoselectivity (d.r. >20:1). To enhance the synthetic utility, we developed a successive cleavage of the two N−O bonds of the resulting heterocycles. A mechanism involving dipolar [3+2] cycloadditions of nitrone intermediates with their tethered alkenes is postulated for formation of these heterocycles.

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