Synthesis of 2-Ethenylcyclopropyl Aryl Ketones via Intramolecular S2-like Displacement of an Ester.

Org Lett

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.

Published: October 2016

The efficient synthesis of trans-2-ethenylcyclopropyl aryl ketones via an intramolecular S2-like displacement of an allylic ester is reported. A novel 1,5-acyl shift process is also observed that contributes to the product mixture. Theoretical calculations provide a rationale for the observed product ratio.

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http://dx.doi.org/10.1021/acs.orglett.6b02588DOI Listing

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