10057-04-2Relevant academic research and scientific papers
HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
, p. 900 - 907 (2021/06/07)
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
Access to Optically Enriched α-Aryloxycarboxylic Esters via Carbene-Catalyzed Dynamic Kinetic Resolution and Transesterification
Liu, Bin,Song, Runjiang,Xu, Jun,Majhi, Pankaj Kumar,Yang, Xing,Yang, Song,Jin, Zhichao,Chi, Yonggui Robin
supporting information, p. 3335 - 3338 (2020/04/30)
Optically active α-aryloxycarboxylic acids and their derivatives are important functional molecules. Disclosed here is a carbene-catalyzed dynamic kinetic resolution and transesterification reaction for access to this class of molecules with up to 99% yields and 99:1 er values. Addition of a chiral carbene catalyst to the ester substrate leads to two diastereomeric azolium ester intermediates that can quickly epimerize to each other and thus allows for effective dynamic kinetic resolution to be realized. The optically enriched ester products from our reaction can be quickly transformed to chiral herbicides and other bioactive molecules.
Copper-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from 2-(o-haloaryloxy)acyl chlorides and primary amines
Hu, Qunxian,Xia, Ziming,Fan, Ling,Zheng, Jiening,Wang, Xiaoxia,Lv, Xin
experimental part, p. 129 - 142 (2012/05/04)
A facile and efficient Cu(I)-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-one derivatives has been developed. The condensation between 2-(o-haloaryloxy)acyl chlorides and primary amines followed by Cu(I)-catalyzed intramolecular C-N bond coupling afforded a variety of 2H-1,4-benzoxazin-3-(4H)-ones in good to excellent yields. Diversified substitutents on the 4-position could be conveniently introduced. ARKAT-USA, Inc.
Enantioselective kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine (iii) species
Uyanik, Muhammet,Yasui, Takeshi,Ishihara, Kazuaki
supporting information; experimental part, p. 2175 - 2177 (2010/06/19)
"Chemical Equation Presented" The iodines(lll) have it: The rational design of a conformationals/ flexible C2symmetric iodosylarene catalyst has been used for the enantioselective Kita oxidative spirolactonization. The reaction occurs through secondary n-σ* or hydrogen-bonding interactions between the chiral catalyst and the substrate. Mes = mesityl (2,4,6-trimethylphenyl).
Chiral hypervalent iodine-catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones
Uyanik, Muhammet,Yasui, Takeshi,Ishihara, Kazuaki
experimental part, p. 5841 - 5851 (2010/09/08)
We demonstrate here the rational design of a conformationally flexible C2-symmetric iodosylarene 8g based on secondary n-σ or hydrogen-bonding interactions as a chiral catalyst for the enantioselective Kita oxidative spirolactonization of 1-nap
