Stereoselective chemical synthesis of carbohydrates constitutes a large and challenging field in modern synthetic organic chemistry.2 Among a wide variety of methodologies for stereoselective construction of polyoxygenated skeletons,3 that being the most straightforward is the stereoselective introduction of two oxygen functionalities to the carbon-carbon double bonds (Scheme I, route a), as represented by the Sharpless epoxidation4 or osmium tetroxide oxidation of allyl alcohols.3h•5 An alternative route may be achieved by anti-Markownikoff hydration of enol ether counterparts (Scheme I, route b), but such an approach has so far been rarely studied.6(1) Silafunctional compounds in organic synthesis. 39.
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