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Synthesis 2023; 55(22): 3777-3792
DOI: 10.1055/a-2126-3774
DOI: 10.1055/a-2126-3774
feature
Access to Symmetrical and Unsymmetrical Cyclobutanes via Template-Directed [2+2]-Photodimerization Reactions of Cinnamic Acids
Autoren
Y.E.T. acknowledges financial support by the GEBIP Award of the Turkish Academy of Sciences.
Abstract
In this work, we have developed a general and broadly applicable template-directed photochemical [2+2]-cycloaddition reaction which provides access to a wide range of symmetrical and unsymmetrical cyclobutane products. The use of 1,8-dihydroxynaphthalene as a covalent template paved the way for successful and highly selective photochemical homodimerization and heterodimerization reactions in the solid state between cinnamic acid derivatives. Notably, the method works equally well with aryl- and heteroaryl-containing substrates leading to the formation of β-truxinic acid analogues as single diastereomers and in high yields (up to 99%).
Key words
cinnamic acids - [2+2] cycloaddition - cyclobutanes - heterodimerization - photochemistry - template-directed synthesis - truxinic acidsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2126-3774.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 31. Mai 2023
Angenommen nach Revision: 10. Juli 2023
Accepted Manuscript online:
10. Juli 2023
Artikel online veröffentlicht:
16. August 2023
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