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Copper-catalyzed [3 + 2] annulation of ethynyl epoxides with malononitrile to access highly substituted dihydrofurans with an all-carbon quaternary stereocenter

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Abstract

An unprecedented copper-catalyzed [3 + 2] annulation with ethynyl epoxides and malononitrile has been described. This reaction provided a direct approach to the access of highly substituted dihydrofurans with an all-carbon quaternary stereocenter bearing a terminal alkynyl group in moderate to good yields, exhibiting excellent atom economy and scalability. The products enabled facile transformations into pyrimidinone and dihydrofuran-fused triazole derivatives.

Graphical abstract: Copper-catalyzed [3 + 2] annulation of ethynyl epoxides with malononitrile to access highly substituted dihydrofurans with an all-carbon quaternary stereocenter

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Publication details

The article was received on 29 Oct 2018, accepted on 03 Dec 2018 and first published on 05 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01168K
Citation: Org. Chem. Front., 2018, Advance Article
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    Copper-catalyzed [3 + 2] annulation of ethynyl epoxides with malononitrile to access highly substituted dihydrofurans with an all-carbon quaternary stereocenter

    X. Li, C. Han, Y. Huang, H. Yao and A. Lin, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO01168K

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