Study of a new ‘chiral proton’ organocatalyst with hydrolase activity: application in azlactone racemic dynamic resolution
作者： Ángel L Fuentes de Arriba , Omayra H Rubio , Luis Simón , Victoria Alcázar , Laura M Monleón
DOI: 10.1016/J.TETASY.2017.04.012
关键词:
摘要: Abstract For the first time, a 1,3-ketoenol system is described as an acid catalyst with hydrolytic activity. The combination of enol and pyridine/benzimidazole supported on benzofuran skeleton allowed creation novel bifunctional organocatalyst, which has been applied in azlactone racemic dynamic resolution. In spite moderate enantioselectivities obtained, constitutes concept field chiral Bronsted catalysis.
sci-hub.se 参考文章(62)
Petri M Pihko, Hydrogen bonding in organic synthesis Wiley-VCH. ,(2009) , 10.1002/9783527627844
Kunru Yu, Xiaohua Liu, Xiaobin Lin, Lili Lin, Xiaoming Feng, Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters Chemical Communications. ,vol. 51, pp. 14897- 14900 ,(2015) , 10.1039/C5CC05534B
Anna Liza B. Valiña, Devleena Mazumder-Shivakumar, Thomas C. Bruice, Probing the Ser-Ser-Lys catalytic triad mechanism of peptide amidase: computational studies of the ground state, transition state, and intermediate. Biochemistry. ,vol. 43, pp. 15657- 15672 ,(2004) , 10.1021/BI049025R
Guojian Lu, Vladimir B. Birman, Dynamic kinetic resolution of azlactones catalyzed by chiral Brønsted acids. Organic Letters. ,vol. 13, pp. 356- 358 ,(2011) , 10.1021/OL102736T
Lunjia Xie, Wenting Hua, Albert S.C Chan, Yun-Chang Leung, Asymmetric alcoholysis of 2-phenyl-5(4 H )-oxazolones by the catalytic mixture of cyclo[( S )-His-( S )-Phe] with chiral auxiliaries Tetrahedron-asymmetry. ,vol. 10, pp. 4715- 4728 ,(1999) , 10.1016/S0957-4166(99)00577-7
Yuxue Liang, Emily B. Rowland, Gerald B. Rowland, Jason A. Perman, Jon C. Antilla, VAPOL phosphoric acid catalysis: the highly enantioselective addition of imides to imines. Chemical Communications. pp. 4477- 4479 ,(2007) , 10.1039/B709276H
Jack Liang, J. Craig Ruble, Gregory C. Fu, Dynamic Kinetic Resolutions Catalyzed by a Planar-Chiral Derivative of DMAP: Enantioselective Synthesis of Protected α-Amino Acids from Racemic Azlactones The Journal of Organic Chemistry. ,vol. 63, pp. 3154- 3155 ,(1998) , 10.1021/JO9803380
Ángel L Fuentes de Arriba, Ángel Gómez Herrero, Omayra H Rubio, Laura M Monleón, Luis Simón Rubio, Victoria Alcázar, Francisca Sanz, Joaquín R Morán, None, Chiral recognition with a benzofuran receptor that mimics an oxyanion hole Organic and Biomolecular Chemistry. ,vol. 13, pp. 493- 501 ,(2015) , 10.1039/C4OB01954G
Takahiko Akiyama, Stronger Brønsted acids Chemical Reviews. ,vol. 107, pp. 5744- 5758 ,(2007) , 10.1021/CR068374J
Rubén Manzano, José M. Andrés, María-Dolores Muruzábal, Rafael Pedrosa, Synthesis of both Enantiomers of Hemiesters by Enantioselective Methanolysis of Meso Cyclic Anhydrides Catalyzed by α-Amino Acid-Derived Chiral Thioureas† Journal of Organic Chemistry. ,vol. 75, pp. 5417- 5420 ,(2010) , 10.1021/JO100792R