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Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes. 2024

Yufen Zheng, and Yueyao Chen, and Yuxuan He, and Antonio Rizzo, and Yuchen Zhou, and Kam-Hung Low, and Elizabeth H Krenske, and Pauline Chiu
The University of Hong Kong, Chemistry, HONG KONG.

Unexpectedly facile dearomative intramolecular (4+3) cycloadditions of thiophenes with epoxy enolsilanes, providing sulfur-bridged cycloadducts, are reported. A total of fifteen thiophene substrates have been found to undergo (4+3) cycloaddition smoothly to produce endo and exo (4+3) adducts in yields of up to 83% with moderate to good diastereoselectivity. Complete conservation of enantiomeric purity was observed when the optically enriched epoxide was used. The desulfurizing transformations of the sulfur-bridged skeleton of the cycloadducts provide functionalized 6,7-fused bicyclic frameworks consisting of 1,3-cycloheptadiene subunits. Density functional theory calculations reveal the origins of the facile dearomatization of thiophenes in these (4+3) cycloadditions.

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