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

作者：Meng, Fei; Zhang, Honglin; Guo, Kang; Dong, Jiayue; Lu, Ai-Min; Zhu, Yingguang^*

来源：Journal of Organic Chemistry, 2017, 82(19): 10742-10747.

DOI：10.1021/acs.joc.7b02133

• C-H CYANATION
• CARBON MULTIPLE BONDS
• BETA-AMINO ACIDS
• UNACTIVATED ALKENES
• SUBSTITUTED ISOXAZOLINES
• INTERMOLECULAR CYANOTRIFLUOROMETHYLATION
• SYNTHETIC APPLICATIONS
• OXIDATIVE CYANATION
• AROMATIC NITRILES
• CYCLIC NITRONES

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)center dot 3H(2)O 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(sp(3))-CN and C-O bonds can be achieved in one step.

• 出版日期2017-10-6
• 单位南京农业大学