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Issue 10, 2019
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Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

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Abstract

A highly chemo- and regioselective [4 + 2] formal cycloaddition of (Z)-3-iodo allylic nucleophiles and allenamides catalyzed by palladium is reported. The methodology proceeds under mild reaction conditions and is tolerant of alkyl and aryl functional groups. The SN2′ substitution at the proximal C[double bond, length as m-dash]C bond performed against the Heck or SN2 pathway delivered a variety of 2-amino-dihydropyrans and 2-amino-tetrahydropiperidines in moderate to satisfactory yields. The [4 + 2] formal cycloaddition derivatives are convertible to interesting scaffolds 2,6,7,7a-tetrahydropyrano[2,3-b]pyrrole and 2,6,7,7a-tetrahydro-1H-pyrrolo[2,3-b]pyridine derivatives via ring-closing metathesis (RCM) with Grubbs catalyst II.

Graphical abstract: Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

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Publication details

The article was received on 11 Dec 2018, accepted on 10 Feb 2019 and first published on 15 Feb 2019


Article type: Communication
DOI: 10.1039/C8OB03072C
Citation: Org. Biomol. Chem., 2019,17, 2651-2656

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    Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

    F. Yan, H. Liang, B. Ai, W. Liang, L. Jiao, S. Yao, P. Zhao, Q. Liu, Y. Dong and H. Liu, Org. Biomol. Chem., 2019, 17, 2651
    DOI: 10.1039/C8OB03072C

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