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Issue 3, 2019
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Nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents

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Abstract

A new nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents was developed, which afforded the corresponding cis-2-alkyl-1,2-dihydronaphthalen-1-ols and 1,2-alkyl amide derivatives in moderate to excellent yields (up to 99% yield) under mild conditions. In this work, we successfully avoided obtaining hydride addition byproducts arising from β-hydride elimination on an ethyl nickel species. Furthermore, a plausible mechanism for the ring-opening reaction was also proposed.

Graphical abstract: Nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents

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Publication details

The article was received on 16 Nov 2018, accepted on 21 Dec 2018 and first published on 04 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02864H
Citation: Org. Biomol. Chem., 2019,17, 703-711
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    Nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents

    Y. Deng, W. Yang, Y. Yao, X. Yang, X. Zuo and D. Yang, Org. Biomol. Chem., 2019, 17, 703
    DOI: 10.1039/C8OB02864H

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