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

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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-11, Vol.53 (89), p.1272-1275
Main Authors: Pagire, Santosh K, Hossain, Asik, Traub, Lukas, Kerres, Sabine, Reiser, Oliver
Format: Article
Language:English
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Summary: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. A visible-light mediated, photocatalyzed strategy for the efficient synthesis of substituted cyclobutanes from cinnamates, styrenes, and chalcones is presented.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc06710k