Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives

作者: Eduardo Busto , Vicente Gotor-Fernández , Vicente Gotor

DOI: 10.1016/J.TETASY.2005.09.006

关键词:

摘要: Abstract Chiral 4-( N , -dimethylamino)pyridine derivatives have been prepared through a chemoenzymatic synthesis where the enzymatic kinetic resolution of family 4-chloro-2-(1-hydroxyalkyl)pyridines is key step for formation potentially important chiral catalysts. Pseudomonas cepacia lipase (PSL) showed excellent enantioselectivity in acylation ( R )-enantiomers E  > 200) using vinyl acetate as acylating agent and THF solvent, obtaining products substrates enantiomerically pure with yields.

参考文章(28)
Edwin Vedejs, Xinhai Chen, Parallel Kinetic Resolution Journal of the American Chemical Society. ,vol. 119, pp. 2584- 2585 ,(1997) , 10.1021/JA963666V
Herman Ziffer, Kenichi Kawai, Masaji Kasai, Mitsuru Imuta, Cleanthis Froussios, Microbially mediated enantioselective ester hydrolyses utilizing Rhizopus nigricans. A new method of assigning the absolute stereochemistry of acyclic 1-arylalkanols Journal of Organic Chemistry. ,vol. 48, pp. 3017- 3021 ,(1983) , 10.1021/JO00166A016
Jun'ichi Uenishi, Kenji Nishiwaki, Shinichiro Hata, Kaoru Nakamura, An optical resolution of pyridyl and bipyridylethanols and a facile preparation of optically pure oligopyridines Tetrahedron Letters. ,vol. 35, pp. 7973- 7976 ,(1994) , 10.1016/0040-4039(94)80025-1
Luis E. Iglesias, Víctor M. Sánchez, Francisca Rebolledo, Vicente Gotor, Candida antarctica B lipase catalysed resolution of (±)-1-(heteroaryl)ethylamines Tetrahedron-asymmetry. ,vol. 8, pp. 2675- 2677 ,(1997) , 10.1016/S0957-4166(97)00330-3
Francesca Bellezza, Antonio Cipiciani, Gabriele Cruciani, Francesco Fringuelli, The importance of ester and alkoxy type functionalities for the chemo- and enantio-recognition of substrates by hydrolysis with Candida rugosa lipase Journal of the Chemical Society, Perkin Transactions 1. pp. 4439- 4444 ,(2000) , 10.1039/B005512N
Mitsuhiro Takeshita, Katsuya Terada, Nami Akutsu, Sachiko Yoshida, Takumi Sato, Synthesis of optically active hetero alkylaryl alcohols by baker's yeast Heterocycles. ,vol. 26, pp. 3051- 3054 ,(1987) , 10.3987/R-1987-12-3051
Eric F. V. Scriven, 4-Dialkylaminopyridines: super acylation and alkylation catalysts Chemical Society Reviews. ,vol. 12, pp. 129- 161 ,(1983) , 10.1039/CS9831200129
J. Craig Ruble, Gregory C. Fu, Chiral pi-Complexes of Heterocycles with Transition Metals: A Versatile New Family of Nucleophilic Catalysts. Journal of Organic Chemistry. ,vol. 61, pp. 7230- 7231 ,(1996) , 10.1021/JO961433G
Gregory C. Fu, Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles. Accounts of Chemical Research. ,vol. 33, pp. 412- 420 ,(2000) , 10.1021/AR990077W
Scott A. Shaw, Pedro Aleman, Edwin Vedejs, Development of chiral nucleophilic pyridine catalysts: applications in asymmetric quaternary carbon synthesis. Journal of the American Chemical Society. ,vol. 125, pp. 13368- 13369 ,(2003) , 10.1021/JA037223K