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Issue 19, 2018
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Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C[double bond, length as m-dash]C bond of indoles

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Abstract

Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.

Graphical abstract: Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C [[double bond, length as m-dash]] C bond of indoles

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Publication details

The article was received on 17 Dec 2017, accepted on 07 Feb 2018 and first published on 07 Feb 2018


Article type: Communication
DOI: 10.1039/C7CC09640B
Citation: Chem. Commun., 2018,54, 2353-2356
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    Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C[double bond, length as m-dash]C bond of indoles

    L. Yu, Y. Zhong, J. Yu, L. Gan, Z. Cai, R. Wang and X. Jiang, Chem. Commun., 2018, 54, 2353
    DOI: 10.1039/C7CC09640B

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