For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO4 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. |
