330460-79-2Relevant academic research and scientific papers
Ligand-Free Copper(I)-Catalyzed Benzylic Acyloxylation of 2-Alkylpyridines under Aerobic Conditions
Cheng, Li,Sun, Yuqian,Wang, Wenrong,Yao, Changsheng,Li, Tuan-Jie
, p. 3074 - 3082 (2019)
A ligand-free copper(I)-catalyzed benzylic acyloxylation of 2-alkylpyridines with carboxylic acids was realized by using 1.0 atm of O2 as a green oxidant. The transformation provided a facile access to a wide range of N-heterocyclic esters thro
Synthesis of 2-Pyridinemethyl Ester Derivatives from Aldehydes and 2-Alkylheterocycle N-Oxides via Copper-Catalyzed Tandem Oxidative Coupling-Rearrangement
Wang, Chang-Sheng,Roisnel, Thierry,Dixneuf, Pierre H.,Soulé, Jean-Fran?ois
supporting information, p. 6720 - 6723 (2017/12/26)
Successful benzylic C(sp3)-H acyloxylation of 2-alkylpyridine, 2-alkylpyrazine, and 2-alkylthiazole compounds was achieved using simple aldehydes. This was carried out via a copper-catalyzed tandem reaction, involving oxidative esterification followed by O-atom transfer of the resultant high yield formed Boekelheide intermediate. The method enables the preparation of functional heterocycles and the desymmetrization of 2,6-dialkylpyridines for efficient synthesis of dissymmetric pincer ligands, thus offering a new life for more practical Boekelheide rearrangement.
The importance of ester and alkoxy type functionalities for the chemo- And enantio-recognition of substrates by hydrolysis with Candida rugosa lipase
Bellezza, Francesca,Cipiciani, Antonio,Cruciani, Gabriele,Fringuelli, Francesco
, p. 4439 - 4444 (2007/10/03)
Racemic esters of 1-phenyl- and 1-(pyridyl)ethyl acetates 1a-c (R = Me, Ph) were subjected to hydrolysis in water in the presence of Candida rugosa lipase (CRL). 1-Pyridylethyl acetates (1, R = Me) are hydrolyzed by crude CRL (C-CRL) and isopropanol (isopropyl alcohol) treated CRL (PT-CRL) at very low rates, and the enantiorecognition was disappointing. By using 1-pyridylethyl benzoates (1, R = Ph) the results differed greatly: hydrolysis occurred much faster, and the enantiorecognition was good for 3- and 4-pyridyl derivatives and excellent for 2-pyridyl derivative. Analogous results were obtained by submitting the 1-phenylethanol esters 4 to enzymatic hydrolysis under the same experimental conditions. The hydrolysis of methyl o-acetoxybenzoates 7 (R = Me) gave quantitatively the deacetylated methyl o-hydroxybenzoates 9 (R = Me) by using either C-CRL or PT-CRL. A complete reversed selectivity is observed in the hydrolysis of phenyl o-acetoxybenzoates 7 (R = Ph) catalyzed by PT-CRL. Molecular modeling studies, aimed at probing the substrate specificity and the enantioselectivity of enzyme in terms of its three-dimensional structure is reported. The Royal Society of Chemistry 2000.
