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Improved organocatalytic electrophilic α-cyanation of β-keto amides with 1-cyanato-4-nitrobenzene
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2018-04-16 , DOI: 10.1016/j.tetlet.2018.04.032
Pran Gopal Karmaker , Jiashen Qiu , Di Wu , Sule Zhang , Hongquan Yin , Fu-Xue Chen

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.



中文翻译:

1-氰基-4-硝基苯对β-酮酰胺的有机催化亲电α-氰化反应的改善

通过使用一种易于获得,安全的新型氰基转移试剂1-cyanato-4-硝基苯,由于增强了结构,大大提高了1-茚满酮衍生的β-酮酰胺的直接亲电子α-氰化的对映选择性。双氢键。因此,在金鸡宁作为双功能有机催化剂存在的情况下,在温和的反应条件下,可以以优异的收率(73-97%)和良好至高的对映选择性(75-91%ee)生产一系列α-氰基β-酮酰胺。

更新日期:2018-04-16
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