title: An anionic C(3)-C(5) ring expansion of beta-ketocyclopropanes to cyclopentenols.
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.
authors.affiliation: Department of Chemistry, University of Adelaide, South Australia, Australia, 5005.
authors.forename: Ben W
authors.initials: BW
authors.lastname: Greatrex
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink