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 GÜLTEKİN

DOI

10.3906/kim-1411-68

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.

First Page

824

Last Page

834

Recommended Citation

GÖKSU, HAYDAR and GÜLTEKİN, MEHMET SERDAR (2015) "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," Turkish Journal of Chemistry: Vol. 39: No. 4, Article 10. https://doi.org/10.3906/kim-1411-68
Available at: https://journals.tubitak.gov.tr/chem/vol39/iss4/10