19019-49-9Relevant academic research and scientific papers
Acyloxylation of cyclic enones: Synthesis of densely oxygenated guaianolides
Marín-Barrios, Rubén,García-Cabeza, Ana Leticia,Moreno-Dorado, F. Javier,Guerra, Francisco M.,Massanet, Guillermo M.
, p. 6501 - 6509 (2014/08/05)
The α′-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.
Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions
Demir, Ayhan S.,Findik, Hamide
, p. 6196 - 6201 (2008/09/21)
The α′-acetoxylation of enones and the α-acetoxylation of aromatic ketones were carried out with potassium permanganate and acetic acid, in which acetoxylation products were obtained in 74-96% yields. The same reaction was carried out with carboxylic acids other than acetic acid, which furnished corresponding acyloxy ketones with the same regioselectivity. For the first time, formyloxylation products were synthesized in a 61-85% yield by using formic acid. The potassium permanganate and acetic acid method was also used for aryl coupling reactions. The reaction of arylboronic acids and arylhydrazines in benzene with potassium permanganate and acetic acid in turn furnished biaryls in 85-96% yield. We have shown that potassium permanganate/carboxylic acid/organic solvent behaves as manganese(III) acetate.
Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones
Demir, Ayhan S.,Reis, ?mer,Igdir, A. Cigdem
, p. 3427 - 3432 (2007/10/03)
Mn(OAc)3 mediated α′-acetoxylation of α,β-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions.
PLE catalysed enantiomeric separation of various (±)-6-acetoxy-α,β-unsaturated cyclic ketones
Tanyeli,Sezen,Dikici,Fleischhauer,Repges,Wang,Gawronski,Kacprzak
, p. 219 - 277 (2007/10/03)
Various (±)-6-acetoxy-α,β-unsaturated cyclic ketones were resolved by PLE catalysed hydrolysis to afford enantiomerically enriched 6-hydroxy derivatives with 85-98% e.e. The absolute configuration of 6-hydroxy-α,β-unsaturated cyclic ketones were determined via CD measurements.
Cleavage of Unsaturated α-Ketols to ω-Oxo-α,β-unsaturated Acids
Floresca, Rey,Kurihara, Masaaki,Watt, David S.,Demir, Ayhan
, p. 2196 - 2200 (2007/10/02)
Sodium periodate is a better reagent than sodium bismutate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated α-ketols and affords ω-oxo-α,β-unsaturated acids in good yield.The combination of this cleavage reaction and a rhodium(I)-m
Hypervalent Iodine Oxidation of α,β-Unsaturated Carbonyl Compounds
Tamura, Yasumitsu,Yakura, Takayuki,Terashi, Hiroaki,Haruta, Jun-Ichi,Kita, Yasuyuki
, p. 570 - 577 (2007/10/02)
Oxidation of non-enolizable α,β-unsaturated carbonyl compounds and enolizable β-monosubstituted α,β-unsaturated carbonyl compounds with phenyl iodine(III) diacetate (PIDA) in methanolic potassium hydroxide gave α-hydroxydimethylacetal β-methoxy products,
