37676-18-9Relevant academic research and scientific papers
Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes
Pagire, Santosh K.,Hossain, Asik,Traub, Lukas,Kerres, Sabine,Reiser, Oliver
, p. 12072 - 12075 (2017)
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.
