Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.
Deluca, Ryan J.,Edwards, Jennifer L.,Steffens, Laura D.,Michel, Brian W.,Qiao, Xiaoxiao,Zhu, Chunyin,Cook, Silas P.,Sigman, Matthew S.
p. 1682 - 1686
(2013/04/10)
Dual Bronsted acid/nucleophilic activation of carbonylimidazole derivatives
Carbonylimidazole derivatives have been found to be highly active acylation reagents for esterification and amidation in the presence of pyridinium salts. These reactions are thought to involve both Bronsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as esters and amides. Finally, the use of pyridinium salts has been shown to accelerate the esterification of carboxylic acids with imidazole carbamates.
Heller, Stephen T.,Fu, Tingting,Sarpong, Richmond
supporting information; experimental part
p. 1970 - 1973
(2012/06/01)
Stereoselective Preparation of (E)-Allyl Alcohols via Radical Elimination from anti-γ-Phenylthio-β-nitro Alcohols
Phenylthio and hydroxymethyl groups may be introduced into nitroalkenes stereoselectively by treatment with benzenethiol and aqueous formaldehyde to give anti-γ-phenylthio-β-nitro alcohols, which are converted into (E)-allyl alcohols via radical elimination induced by Bu3SnH.
Kamimura, Akio,Ono, Noboru
p. 1278 - 1280
(2007/10/02)
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