34361-69-8Relevant 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 the allylic hydroperoxides catalyzed by zeolite-confined osmium(0) nanoclusters
G?ksu, Haydar,Dalmizrak, Di?dem,Akbayrak, Serdar,Gültekin, Mehmet Serdar,?zkar, Saim,Metin, ?nder
, p. 142 - 147 (2013/08/23)
A facile, efficient and eco-friendly method for the one-pot synthesis of 1,2/3-triols from the allylic hydroperoxides were developed by using zeolite-confined osmium(0) nanoclusters as reusable catalyst and without using any co-oxidant (H2Osub
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
experimental part, 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.
Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA
Donohoe, Timothy J.,Blades, Kevin,Moore, Peter R.,Waring, Michael J.,Winter, Jon J. G.,Helliwell, Madeleine,Newcombe, Nicholas J.,Stemp, Geoffrey
, p. 7946 - 7956 (2007/10/03)
The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.
The directed dihydroxylation of allylic alcohols
Donohoe, Timothy J.,Moore, Peter R.,Waring, Michael J.,Newcombe, Nicholas J.
, p. 5027 - 5030 (2007/10/03)
The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydroge
