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Issue 85, 2018
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Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

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Abstract

A copper-catalyzed asymmetric propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones as C,O-bisnucleophiles through the desilylation-activated strategy has been developed. With the catalysis of Cu(OAc)2·H2O in combination with a chiral tridentate P,N,N-ligand, the reaction displayed a broad substrate scope, and thus provided a variety of chiral dihydropyrano[2,3-c]pyrazoles in high yields and with excellent enantioselectivities (up to 96% ee).

Graphical abstract: Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

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Publication details

The article was received on 14 Jul 2018, accepted on 28 Sep 2018 and first published on 29 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC05706K
Citation: Chem. Commun., 2018,54, 12033-12036
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    Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

    L. Li, Z. Liu and X. Hu, Chem. Commun., 2018, 54, 12033
    DOI: 10.1039/C8CC05706K

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