Exploratory study demonstrates photocatalytic cycloaddition enables efficient synthesis of functionalized compounds, suggesting potential in organic synthesis.
In this study, we report an exploratory study on the reductive cyclization of nitrogen- and oxygen-containing aryl bisenones, enabling the efficient synthesis of highly functionalized pyrrolidines and tetrahydrofurans under visible-light irradiation. The transformation proceeds through a photocatalytic [2+2] cycloaddition promoted by catalytic amounts of Eosin Y, with Schreiner’s thiourea and Hantzsch ester acting as mediators under visible green light irradiation. The transformation showed to be stereoselective and affords the five-membered heterocycle as a single, trans isomer. Moreover, the introduction of chiral oxazolidinone auxiliaries onto aryl bisenone precursors allowed the formation of chiral, highly substituted trans pyrrolidines and tetrahydrofurans in good yields, although with modest stereoselectivities.
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Franco et al. (2025) studied this question.
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