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Synthesis of Cyclopentenones from Cyclopropanes and Silyl Ynol Ethers

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  • Financial support was provided by the NIGMS (grant no. GM074822) and the Welch Foundation.

Abstract

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Exploiting an opening: Lewis acid promoted ring-opening of donor–acceptor cyclopropanes generates a 1,3-zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri-, tetra-, and penta-substituted cyclopentenones in high yield.

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