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Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

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Abstract

An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong π–π-stacking of arene moieties, whereas diastereoselectivity relies on the electronic effects or ortho-substitution of the arene substrate. The utility of this transformation is demonstrated by the formal synthesis of the lignane natural product (±)-Tanegool.

Graphical abstract: Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

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Publication details

The article was received on 27 Aug 2017, accepted on 06 Oct 2017 and first published on 06 Oct 2017


Article type: Communication
DOI: 10.1039/C7CC06710K
Citation: Chem. Commun., 2017, Advance Article
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    Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

    S. K. Pagire, A. Hossain, L. Traub, S. Kerres and O. Reiser, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC06710K

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