One approach to improving the selectivity of peroxide installation is the Mukaiyama peroxidation . Mukaiyama peroxidation and other Mukaiyama-type functionalizations can occur in the presence of indoles and electron-rich arenes, selectively functionalizing less electron-rich alkenes. Baran demonstrated the practical hydroamination of alkenes with nitroarenes, using Fe conditions on substrates with a variety of heterocycles present 6 . Renata chemoselectively functionalized an alkene with Mn(dpm)3 in the presence of lactam and methoxybenzene groups to generate a 5-deoxyterreulactone C precursor . Carreira performed an intramolecular cyclization/alkene hydration with cobalt as the catalyst, a method that tolerated the presence of a pyrrole . Boger utilized FeCl3 in the oxidation and functionalization of an alkene to form 20'vinblastine analogues, demonstrating selectivity of Fe catalyzed conditions to target alkenes over indoles . In route to the syntheses of Kopsia alkaloids, Magnus successfully oxidized an α,βunsaturated ester to the corresponding α-hydroxy ester using Mn(dpm)3 as a catalyst, in the presence of indoline heterocycles. Herzon performed intermolecular hydropyridylation with cobalt and pyridine salts, showing that pyridine-containing products would, in fact, be stable under Co catalyzed conditions . Within our group, Mukaiyama conditions were used to hydrate the alkene within a route to principinol D . Given the wide range of alkene substrates tolerant to Mukaiyama-type hydrations, there was an opportunity to develop a method of hydrodealkenylation that utilized such chemistry and would facilitate future multistep synthesis endeavors. We hypothesized that hydrodealkenylation could be accomplished utilizing Mukaiyama-type conditions for peroxide installation followed by Fe(II) promoted βfragmentation (Fig. ).