Metal homoenolates represent uniquely useful organometallic intermediates in synthetic chemistry, allowing umpolung synthesis of beta-functionalized carbonyl compounds. While siloxycyclopropanes had been established as reliable precursors to homoenolates, often stoichiometric, for diverse carbon-carbon bond forming reactions, unprotected cyclopropanols have emerged as alternative and attractive precursors to homoenolates, often catalytically generated, in carbon-carbon and carbon-heteroatom bond-forming reactions. This review article provides an overview of the development of such homoenolate transformations, as classified with respect to the metals involved in the cyclopropane ring opening.