Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor–Acceptor–Acceptor Cyclopropanes

Abstract

A study of cyclopropanations of oxy-substituted ethenes with ethyl α-aroyl-α-diazoacetates is described. The reaction of ethyl α-aroyl-α-diazoacetates with trimethylsilyl vinyl ether or ethyl vinyl ether gave dihydrofuran products, but when vinyl acetate was used the products were stable cyclopropanes, ethyl 2-acetoxy-1-aroylcyclopropanecarboxylates, which were isolated in 16–87% yield depending on the nature and position of the aryl-ring substituent.

Key words

cyclopropanations - donor–acceptor–acceptor - rhodium catalyst - β-lactones - dihydrofurans

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