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Redox-neutral carbon–carbon (C–C) bond activation and functionalization strategies of cyclopropanols that give metallo homoenolate have offered merits to construct a range of useful β-functionalized ketones in an inverse-polarity fashion. Discovery and identification of oxidative C–C activation reactions of cyclopropanols that generate metallo enolate–homoenolate would provide an opportunity to afford α,β-difunctionalized ketones. We report catalytic, net oxidative C–C activation, and silylation of cyclopropanols with traceless acetal directing groups under consecutive Ir and Rh catalysis in regio-, stereo-, and chemo-selective fashion. In detail, Ir-catalyzed hydrosilylation of cyclopropyl acetates provides the acetal directing group in quantitative yield. Rh-catalyzed proximal C–C silylation of the resulting cyclopropyl silyl acetal produces the metallo enolate–homoenolate equivalent, dioxasilepine, which uniquely holds an interconnected β-silyl moiety and Z-vinyl acetal. Upon sequential treatment of a silaphile that removes the acetal directing group and electrophile, the seven-membered silicon-containing heterocycle, serving as the ketone α,β-dianion equivalent, delivers α,β-difunctionalized ketones. Scope of the hitherto unexplored reactivity of cyclopropanols toward net oxidative C–C silylation and the versatility of the resulting dioxasilepines were demonstrated. These include late-stage, net oxidative C–C silylation of biologically relevant molecules and facile production of a range of α,β-difunctionalized ketones. Preliminary mechanistic studies suggest that the C–C activation harnessing the electron-rich Wilkinson-type catalyst is likely the turnover-determining step and a Rh-π interaction is the key to the efficient metal insertion to the proximal C–C bond in cyclopropanols.