62365-17-7Relevant academic research and scientific papers
Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO4 and chiral cinchona ligands in the absence of co-oxidant
G?ksu, Haydar,Gültekin, Mehmet Serdar
, p. 824 - 834 (2015/08/06)
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.
One-pot synthesis of 1,2,3-triols from allylic hydroperoxides and a catalytic amount of OsO4 in aqueous acetone
Alp, Cemalettin,Atmaca, Ufuk,?elik, Murat,Gültekin, Mehmet Serdar
scheme or table, p. 2765 - 2768 (2010/02/28)
Allylic hydroperoxides were converted into the corresponding triols in the presence of a catalytic amount of OsO4. The present reaction involves regeneration of active osmium species by the hydroperoxide functionality and occurs in a diastereoselective manner to form triols in high yields. A plausible mechanism for the formation of 1,2,3-triols from allylic hydroperoxide is presented.
ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS. EMPIRICAL RULE
Cha, J. K.,Christ, W. J.,Kishi, Y.
, p. 2247 - 2256 (2007/10/02)
An empirical formulation is presented to predict the stereochemistry of major osmylation products of allylic alcohols and their derivatives.
