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  • Title: Stereoselective OsO4-catalyzed oxidative cyclization of 1,5-dienes.
    Author: Poethig A, Strassner T.
    Journal: J Org Chem; 2010 Mar 19; 75(6):1967-73. PubMed ID: 20180518.
    Abstract:
    The mechanism of the oxidation of 1,5-dienes with osmium tetroxide was investigated by density functional theory calculations (B3LYP/6-311+G*). The observed products, 2,5-bis(hydroxymethyl)tetrahydrofurans, are formed stereoselectively in a concerted reaction. Enantioselectivity could be induced by an enantioselective dihydroxylation followed by condensation of the 5,6-dihydroxyolefine with osmium tetroxide, while the diastereoselectivity is achieved by reaction of the 1,5-diene with osmium tetroxide and intermediate reoxidation of the osmium(VI) ester.
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