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An enantioselective three-component rearrangement of alkenylfurans with various cycloalkyl silyl peroxides and anilines has been developed by merging photoredox catalysis with chiral Brønsted acid catalysis. This protocol provides expedient access to a broad spectrum of ketoalkyl-functionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities. Diverse functional groups can be introduced via facile product derivations.