Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene |
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| Authors: | Pran Gopal Karmaker Jiashen Qiu Di Wu Sule Zhang Hongquan Yin Fu-Xue Chen |
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| Institution: | School of Chemistry & Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, China |
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| Abstract: | By using a readily accessible, new and safe cyano-transfer reagent, 1-cyanato-4-nitrobenzene, the enantioselectivity of the direct electrophilic α-cyanation of 1-indanone-derived β-keto amides was greatly improved as a result of an enhanced double-hydrogen bonding. Thus, in the presence of cinchonine as the bifunctional organocatalyst, a series of α-cyano β-keto amides were produced in excellent yields (73–97%) and good to high enantioselectivities (75–91% ee) under mild reaction conditions. |
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| Keywords: | Asymmetric catalysis Cinchona alkaloids β-Ketoamides Nitriles Organocatalysis |
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