title: Copper-Catalyzed Three-Component Annulations of Alkenes, Nitrosoarenes, and N-Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles.
abstract: One-pot cascade annulations among nitrosoarenes, alkenes, and N-hydroxyallylamines have been achieved with CuCl/O2catalysts, 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.
authors.affiliation: Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan.
authors.forename: Rahul Kisan
authors.initials: RK
authors.lastname: Kawade
authors.affiliation: Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan.
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu
keywords: amino alcohols; annulations; copper catalysis; dipolar [3+2]-cycloadditions; heterocycles