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NaOH/BEt3 Catalyzed Regioselective Hydroboration of Epoxides with HBpin to Secondary Alcohols

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The regioselective hydroboration/hydrolysis of epoxides with pinacolborane to secondary alcohols catalyzed by NaOH/BEt3 was achieved. Glycidyl oxide, styrene oxide and adamantane epoxide underwent facile hydroboration/deprotection to provide secondary alcohols with exclusive selectivity in good to excellent yields. Moreover, the stereochemistry of epoxides could also be well retained and delivered the corresponding secondary alcohols with high optical activity under alkaline catalytic system. Significantly, in this reaction, diverse functional groups can be compatible, including hydrogenation-sensitive groups, such as carbon-carbon double bond and halogen.

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