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This manuscript describes the use of alcohol-derived sulfamate ester anchors to guide the alkylation of aliphatic C(3)–H bonds in the course of Giese reactions. This reaction tolerates a large range of functional groups that are sensitive to oxidation. The developed reaction proceeds with predictable diastereoselectivity using enantioenriched radical acceptors, and complex small molecule substrates. Surprisingly, this transformation affects position-selective alkylation of tertiary and secondary centers with synthetically useful efficiencies.