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

doi:10.6023/cjoc202002012

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, 茚

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

引用此文

张阳, 邢芬, 冯泽男, 杜广芬, 顾承志, 何林. 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[J]. 有机化学, 2020, 40(6): 1608-1617.

Zhang Yang, Xing Fen, Feng Zenan, Du Guangfen, Gu Chengzhi, He Lin. N-Heterocyclic Carbene-Catalyzed Double Michael Addition of Cyano Acetates and Dienones: Diastereoselective Synthesis of Multisubstituted Cyclohexanones and Indanes[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1608-1617.

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