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Access to Symmetrical and Unsymmetrical Cyclobutanes via Template-Directed [2+2]-Photodimerization Reactions of Cinnamic Acids

Bilge Banu Yagci, Badar Munir, Yunus Zorlu, Yunus Emre Türkmen*

*Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye, Email: yeturkmenbilkent.edu.tr

B. B. Yagci, B. Munir, Y. Zorlu, Y. E. Türkmen, Synthesis, 2023, 55, 3777-3792.

DOI: 10.1055/a-2126-3774


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Abstract

The use of 1,8-dihydroxynaphthalene as a covalent template enables highly selective photochemical reactions in the solid state between cinnamic acid derivatives to provide β-truxinic acid analogues as single diastereomers in high yields. The cycloadducts are hydrolyzed easily under basic conditions at room temperature in excellent yields.


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Note

Out of the six examples shown, four were published in our previous communication on this reaction: J. Org. Chem., 2021, 86, 13118. DOI: 10.1021/acs.joc.1c01534

Yunus Emre Türkmen, July 26, 2024


Key Words

cinnamic acids, [2+2] cycloaddition, cyclobutanes, heterodimerization, photochemistry


ID: J66-Y2023