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Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions

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Abstract

A novel and efficient synthesis of diversely functionalized cyclopentene derivatives through the multicomponent reactions of 1,2-allenic ketones with 4-chloroacetoacetate and malononitrile/cyanoacetate under mild and metal-free conditions is presented. Mechanistically, the formation of title compounds involves a cascade process including nucleophilic substitution, Michael addition and intramolecular aldol type reaction. Interestingly, when 1-phenyl allenic ketones bearing electron-donating groups on the phenyl ring were reacted with 4-chloroacetoacetate and cyanoacetate, methylenecyclo-pentanes, the regioisomer of cyclopentenes, were formed with good selectivity and high efficiency.

Graphical abstract: Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions

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Publication details

The article was received on 12 Sep 2018, accepted on 02 Nov 2018 and first published on 03 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02259C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions

    Q. Wang, T. Zhang, Y. Fan and X. Fan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02259C

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