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Issue 13, 2014
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Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents

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Abstract

A new platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with various Grignard reagents was reported, which afforded the corresponding anti-2-substituted-1,2-dihydronaphthalen-1-ol products with moderate to good yields in the presence of a catalytic amount of Pt(PPh3)4 (2.5 mol%) under mild conditions. The effects of catalyst loading, solvent and temperature on the yield were also investigated. Furthermore, the trans-configuration of the product 5i was confirmed by X-ray diffraction analysis.

Graphical abstract: Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents

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Publication details

The article was received on 06 Nov 2013, accepted on 23 Jan 2014 and first published on 24 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42199F
Citation: Org. Biomol. Chem., 2014,12, 2080-2086
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    Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents

    D. Yang and N. Liang, Org. Biomol. Chem., 2014, 12, 2080
    DOI: 10.1039/C3OB42199F

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