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Copper‐Catalyzed Three‐Component Annulations of Alkenes, Nitrosoarenes, and N‐Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles
Author(s) -
Kawade Rahul Kisan,
Liu RaiShung
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611388
Subject(s) - nitrone , chemistry , catalysis , cleavage (geology) , cycloaddition , combinatorial chemistry , copper , alkene , organic chemistry , stereochemistry , materials science , fracture (geology) , composite material
One‐pot cascade annulations among nitrosoarenes, alkenes, and N‐hydroxyallylamines have been achieved with CuCl/O 2 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.