Symmetrical/Unsymmetrical Cyclobutanes via Cinnamic Acids Photodimerization

Access to Symmetrical and Unsymmetrical Cyclobutanes via Template-Directed [2+2]-Photodimerization Reactions of Cinnamic Acids: B. B. Yagci, B. Munir, Y. Zorlu, Y. E. Türkmen
Synthesis 2023, DOI: 10.1055/a-2126-3774

Densely functionalized cyclobutanes are fascinating and important compounds, whose efficient regio- and stereo-controlled synthesis still poses challenges to organic chemists. The photochemical [2+2] cycloaddition of suitably functionalized olefins represents a viable entry to the title compounds, and recently a study from the group of Professor Yunus E. Türkmen from Bilkent University (Ankara, Türkiye) shed further light on the reaction, by focussing on cinnamic acids as starting materials.

Professor Türkmen said: “In this work, we took advantage of the unique chemical and geometrical features of 1,8-dihydroxynaphthalene as a template molecule and developed a general solution to the longstanding problem of selective photochemical homo- and heterodimerization of cinnamic acids to give symmetrical and unsymmetrical cyclobutanes with full diastereocontrol.”

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