85866-03-1Relevant articles and documents
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.
From common carbohydrates to enantiopure cyclooctane polyols and glycomimetics via deoxygenative zirconocene ring contraction
Paquette, Leo A.,Zhang, Yunlong
, p. 4353 - 4363 (2007/10/03)
D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rea
Enantioselective route from carbohydrates to cyclooctane polyols
Paquette, Leo A.,Zhang, Yunlong
, p. 511 - 513 (2007/10/03)
(Chemical Equation Presented) A synthetic route to select cyclooctane-1,2,3-triols and 1,2,3,4,5-pentaols has been defined. The starting materials are D-glucose or D-arabinose, and the key steps consist of a zirconocene-promoted ring contraction, a [3,3]
Synthesis of Stereoisomeric Medium-Ring α,α′-Dihydroxy Cycloalkanones
Paquette, Leo A.,Hartung, Ryan E.,Hofferberth, John E.,Vilotijevic, Ivan,Yang, Jiong
, p. 2454 - 2460 (2007/10/03)
The stereochemical course of the epoxidation of the silyl enol ethers of 2-tert-butyldimethylsilyl-oxycycloheptanone and -cyclooctanone has been investigated and shown to proceed exclusively anti to the existing α-substituent. 2-(Benzyloxy)cyclooctanone b
Chemical consequences of the ground-state conformations of cyclooctyl rings. Examples of reactivity differences in α-hydroxy and α,α′-dihydroxy eight-membered cyclic ketones
Paquette, Leo A.,Hartung, Ryan
, p. 1201 - 1208 (2007/10/03)
A program directed toward the elucidation of various conformational factors that control reactivity differences in cyclooctyl and cyclooctenyl systems is described. This overview reports on the divergent reactivity observed in the alkylation of saturated
