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An anionic C(3)-C(5) ring expansion of beta-ketocyclopropanes to cyclopentenols
Ben W Greatrex1, Dennis K Taylor, Edward R T Tiekink
1Department of Chemistry, University of Adelaide, South Australia, Australia, 5005.
Organic Letters
|February 14, 2002
Abstract:
[reaction: see text] When treated with base, beta-ketocyclopropylcarboxylates ring-open to initially afford either cis or trans alpha,beta-unsaturated ketones. The cis isomer undergoes an intramolecular aldol reaction to afford allylic cyclopentenols in high yield and excellent diastereoselectivity. Choice of base is key to a successful outcome.