Copper‐Catalyzed Three‐Component Annulations of Alkenes,Nitrosoarenes, and N‐Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles |
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Abstract: | One‐pot cascade annulations among nitrosoarenes, alkenes, and N‐hydroxyallylamines have been achieved with CuCl/O2 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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Keywords: | amino alcohols annulations copper catalysis dipolar [3+2]-cycloadditions heterocycles |
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