Abstract
We describe a highly diastereo- and enantioselective two-step formal anti-Markovnikov addition of H2O to diastereomeric mixtures of olefins. Our approach relies on the highly enantioselective syn-specific Shi-epoxidation of both olefin isomers and a stereoconverging epoxide hydrosilylation featuring a directional isomerization step via a configurationally labile radical intermediate that is reduced by a syn-selective intramolecular hydrogen atom transfer from a Ti-H bond.
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