Access to Cyano-Containing Isoxazolines via Copper-Catalyzed Domino Cyclization/Cyanation of Alkenyl Oximes

A highly
efficient copper-catalyzed cyclization/cyanation cascade
of unactivated olefins bearing oximes is described. A variety of cyano-containing
isoxazolines have been obtained in high yields with cheap Cu­(NO3)2·3H2O as the catalyst and TMSCN
as the non-metallic cyanide source. The present method provides a
mild, simple, and practical access to cyano-substituted isoxazolines
and is amenable to gram scale. The simultaneous construction of C­(sp3)–CN and C–O bonds can be achieved in one step.