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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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Supplementary files

Article information


Submitted
11 Dec 2018
Accepted
10 Feb 2019
First published
15 Feb 2019

Org. Biomol. Chem., 2019,17, 2651-2656
Article type
Communication

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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