The [4 + 3] cycloaddition of the oxyallyl intermediates, derived from 2-chlorocyclohexanone and related compounds, to cyclic 1,3-dienes under the Fohlisch conditions (Et(3)N in CF3CH2OH) has been examined to assess its scope and limitations. Effects of substitution with alkyl or alkoxy groups on the cyclohexanone ring, along with variations of the base, solvent, or ring size have been investigated. Also included is a comparison between the Fohlisch cycloaddition and the Schmid cycloaddition (utilizing alpha’-chloroenamines). These reactions of cyclic oxyallyls afford tricyclic or tetracyclic cycloadducts of considerable molecular complexity with a well-defined stereochemical outcome and, thus, represent a new synthetic route to functionalized medium-sized carbocycles and heterocycles.