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氮杂环卡宾催化氰基乙酸酯与二烯酮双Michael反应:非对映选择性合成多取代环己酮和茚

本站小编 Free考研考试/2022-02-14

摘要/Abstract



利用氮杂环卡宾(NHC)独特的Brønsted碱性催化二烯酮与氰基乙酸酯的双Michael加成反应.在10 mol% NHC催化下,二乙烯酮可以与氰基乙酸酯反应,以60%~89%的产率和5:1~>20:1的dr值得到多取代环己酮.在相同反应条件下,邻苯二烯酮与氰基乙酸酯和丙二腈等反应,以77%~98%的产率和>20:1的dr值得到多取代茚产物.
关键词: 氮杂环卡宾, Michael加成, Brønsted碱, 环己酮,
The unique Brønsted basic character of N-heterocyclic carbenes (NHCs) has been used to catalyze the double Michael addition between dienones and cyanoacetates. In the presence of 10 mol% NHC, divinyl ketones reacted with cyano acetates to produce multisubstituted cyclohexanones in 60%~89% yields with 5:1~>20:1 dr. Under the same conditions, benzenedi(enones) underwent double Michael addition with cyano acetates or malononitrile to construct multisubstituted indanes in 77%~98% yields and >20:1 dr.
Key words: N-heterocyclic carbenes, Michael addition, Brønsted base, cyclohexanone, indane


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