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

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 acids

Publication History

Received: 31 May 2023

Accepted after revision: 10 July 2023

Accepted Manuscript online:
10 July 2023

Article published online:
16 August 2023

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