New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid

Add time:07/13/2019    Source:sciencedirect.com

Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by the sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

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