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We describe a highly diastereo‐ and enantioselective two‐step formal anti‐Markovnikov addition of H2O to diastereomeric mixtures of trisubstituted olefins. Our approach overcomes the limits of classical stereospecific addition reactions to olefins for the generation of adjacent stereocenters. In these stereospecific reactions, separation of olefin diastereomers is essential. Our method circumvents...