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Nitrostyrenes as 1,4-CCNO-dipoles: diastereoselective formal [4+1] cycloaddition of indoles

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Abstract

An unusual reactivity of nitrostyrenes in phosphorous acid was discovered, which permits the employment of these readily available synthons as 1,4-CCNO-dipole surrogates in a highly diastereoselective (4+1)-cycloaddition of indoles to afford 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically pure form.

Graphical abstract: Nitrostyrenes as 1,4-CCNO-dipoles: diastereoselective formal [4+1] cycloaddition of indoles

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Publication details

The article was received on 13 Sep 2018, accepted on 05 Nov 2018 and first published on 06 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07451H
Citation: Chem. Commun., 2018, Advance Article
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    Nitrostyrenes as 1,4-CCNO-dipoles: diastereoselective formal [4+1] cycloaddition of indoles

    A. V. Aksenov, N. A. Aksenov, D. A. Aksenov, V. F. Khamraev and M. Rubin, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC07451H

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