High-yielding oxidation of β-hydroxyketones to β-diketones using o-iodoxybenzoic acid.

نویسندگان

  • Samuel L Bartlett
  • Christopher M Beaudry
چکیده

The oxidation of β-hydroxyketones to β-diketones was systematically investigated. o-Iodoxybenzoic acid (IBX) was found to be efficient, operationally easy, and superior to other common oxidants. The reaction is suitable for milligram- to gram-scale oxidations.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Albumin-directed stereoselective reduction of 1,3-diketones and β-hydroxyketones to anti diols.

The reduction of 1,3-diketones and β-hydroxyketones with NaBH(4) in aqueous acetonitrile is highly stereoselective in the presence of stoichiometric amounts of bovine or human albumin, giving anti 1,3-diols with d.e. up to 96%. The same reaction, without albumin, gives syn and anti 1,3-diols in approximately 1:1 ratio. The presence of an aromatic carbonyl group is essential for diastereoselecti...

متن کامل

QM/MM Study on the Mechanism of Aminophenol Oxidation by Functionalized β-Cyclodextrin as Oxidase Nanomimic

In this study, functionalized β-cyclodextrin (β-CD) by aldehyde group was investigated as an oxidase enzyme mimic for the amino phenol oxidation. All calculations were performed by GAUSSIAN 09 package using two layers ONIOM method at the ONIOM (MPW1PW91/6-311++G(d,p)/UFF) level. In the first step, H2O2 is encapsulated in the hydrophobic cavity. In the second step, H2<...

متن کامل

Chemical Constituents from the Stem Barks of Plumeria rubra L.

Background and objectives: Plumeria rubra L. (Apocynaceae) is a deciduous shrub or small tree cultivated in subtropical and tropical countries.  Its bark is prescribed to treat amoebic dysentery,   dropsy, jaundice, scabies, gonorrhea, venereal affections and wounds. In the present research, we aimed to isolate and identify the chemical constituents of the bark of ...

متن کامل

Cytotoxicity of ruthenocene-containing β-diketones.

BACKGROUND Ferrocene-containing β-diketones and cisplatin, [(NH(3))(2)PtCl(2)], possess strong antineoplastic activity. No information is available regarding the anticancer activity of the corresponding ruthenocene complexes. This study examined the cytotoxicity of stable ruthenocene-containing β-diketones. The results were related to the cytotoxicity of cisplatin and the ease of ruthenium elec...

متن کامل

Enantioselective Evans-Tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate.

Lithium diphenylbinaphtholate catalyzed the enantioselective Evans-Tishchenko reduction of achiral β-hydroxyketones to afford monoacyl-protected 1,3-diols with high stereoselectivities. In the reaction of racemic β-hydroxyketones, kinetic optical resolution occurred in a highly stereoselective manner.

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • The Journal of organic chemistry

دوره 76 23  شماره 

صفحات  -

تاریخ انتشار 2011