N-Heterocyclic Carbene-Catalyzed Double Michael Addition of Cyano Acetates and Dienones: Diastereoselective Synthesis of Multisubstituted Cyclohexanones and Indanes

doi:10.6023/cjoc202002012

Abstract

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

Cite this article

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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