Li Qing-Hua, Li Zhao-Feng, Tao Jing, Li Wan-Fang, Ren Li-Qing, Li Qian, Peng Yun-Gui, Liu Tang-Lin
School of Chemistry and Chemical Engineering , Southwest University , Chongqing 400715 , China.
College of Science , University of Shanghai for Science and Technology , Shanghai 200093 , China.
Org Lett. 2019 Oct 18;21(20):8429-8433. doi: 10.1021/acs.orglett.9b03194. Epub 2019 Oct 8.
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.
α-氨基腈是天然产物中的重要结构单元和有机化学中的关键中间体。在此,开发了一种氰醇与氨直接胺化合成N-未保护的α-氨基腈的方法。该反应通过钛催化的氰基转移反应进行,具有高原子经济性和操作简单的特点。多种酮或醛氰醇与氨都能兼容,并且在温和的反应条件下以中等到高的产率合成了N-未保护的α-氨基腈。