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

Authors : Haydar Göksu, Mehmet Serdar Gültekin

Pages : 824-841

Doi:10.3906/kim-1411-68

View : 17 | Download : 11

Publication Date : 9999-12-31

Article Type : Makaleler

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.