Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO$_{4}$ and chiral cinchona ligands in the absence of co-oxidant


Abstract: For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO$_{4}$ and chiral cinchona alkaloid derivatives in an acetone-water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.

Keywords: Chiral 1/2, 3-triols, chiral cinchona alkaloids derivatives, allylic hydroperoxide, intramolecular atom transfer.

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