1129-30-2Relevant articles and documents
Controlled synthesis of 2-acetyl-6-carbethoxypyridine and 2,6-diacetylpyridine from 2,6-dimethylpyridine
Su, Biyun,Zhao, Jianshe,Cui, Yong,Liang, Yongqing,Sun, Wenhua
, p. 2317 - 2324 (2005)
The controlled syntheses of mono- and bis-acetylpyridine from the same starting material (2,6-dimethylpyridine) are reported, including the asymmetrical compound 2-acetyl-6-carbethoxypyridine, which has not before been reported. The influences of the amount of catalyst EtONa and the reaction conditions to the final products are also explored. A modification of the reported preparation for the 2,6-dipicolinic acid, 2,6-dicarbethoxypyridine and 2,6-diacetylpyridine with higher purity and improved yields is provided here, and the physical and spectral properties of these products are identical to those reported in the literature. Copyright Taylor & Francis, Inc.
A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
supporting information, p. 3031 - 3035 (2018/06/27)
An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).
Organopromoted Selectivity-Switchable Synthesis of Polyketones
Liu, Jie,Hu, Kang-Fei,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 5593 - 5596 (2017/10/25)
In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.