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Compared with conventional ionic pathways that require stringent polarity matching and substrate prefunctionalization, the present strategy employs alkyl halides as radical precursors, wherein photoredox mediated single electron transfer (SET) generates radicals that undergo radical addition to non\u2010polarized alkenes followed by C\u2013O bond formation. High stereocontrol and efficiency are achieved through a carboxylate\u2010coordinated chiral copper complex (up to 83% yield, up to 96% e.e., &gt;20:1 d.r.). The synthetic utility is demonstrated by the late\u2010stage diversification of bioactive molecules. 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