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Tuning Vinylethylene Carbonates into [4 + 2] Cycloaddition via Silylation and Vinylogous Peterson Elimination
Wei Feng1, Li Xu1, Deng-Yuan Li1
1Shanghai Key Laboratory of Functional Materials Chemistry, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Key Laboratory for Advanced Materials and School of Chemistry and Molecular Engineering, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, China.
Abstract:
Vinylethylene carbonates have been extensively used to trigger [3 + n] or [5 + n] cycloaddition via the formation of η3-allylic intermediates, while the important [4 + n] cycloaddition has not been explored yet. Here, we report a new strategy to convert vinylethylene carbonates into 4-(trimethylsilyl)but-2-en-1-ols, which can readily undergo [4 + 2] cycloaddition by in situ formation of 1,3-dienes. This novel reaction involves [PdII]-catalyzed decarboxylative silylation, [FeIII]-catalyzed vinylogous Peterson elimination, and subsequent [4 + 2] cycloaddition to afford a multisubstituted cyclohexa-1,4-diene skeleton.
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