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http://dx.doi.org/10.5012/bkcs.2003.24.9.1269

Lipase-catalyzed Remote Kinetic Resolution of Quaternary Carbon-containing Alcohols and Determination of Their Absolute Configuration  

Im, Dai-Sig (Computer-aided Molecular Design & Bioscience Research Co., Ltd.)
Cheong, Chan-Seong (Life Science Divistion, Korea Insitute of Science and Technology)
Lee, So-Ha (Life Science Divistion, Korea Insitute of Science and Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.24, no.9, 2003 , pp. 1269-1275 More about this Journal
Abstract
The quaternary carbon-containing alcohols (1-6) were resolved enantioselectively by various lipases such as PFL (Pseudomonas fluorescens lipase), LAK (Pseudomonas fluorescens lipase), CRL (Candida rugosa lipase) and PCL (Pseudomonas cepacia lipase). The enzymatic resolution of racemic alcohol $({\pm})-2$ gave the excellent enantioselectivity in favor of (S)-2d in 99% ee, while those of the racemic alcohols (1, 3, 4, 5 and 6) gave the resolved alcohols with moderate to good enantioselectivity. Also, their absolute configurations were determined by chemical transformation to the known compounds.
Keywords
Chiral tertiary nitriles; Lipase; Enantioselective; Resolution;
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1 Pogorevc, M.; Faber, K. J. Mol. Cat. B: Enzymatic 2000, 10,357.   DOI   ScienceOn
2 Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S. Tetrahedron Lett. 1981, 22, 4107.   DOI   ScienceOn
3 Zoltewicz, J.A. Top. Curr. Chem. 1975, 59, 33.   DOI
4 Im, D. S.; Cheong, C. S.; Lee, S. H.; Park, H.; Youn, B. H.Tetrahedron: Asymmetry 1999, 10, 3759.   DOI   ScienceOn
5 Hartmann, R. W.; Batzl, C. J. Med. Chem. 1986, 29, 1362.   DOI
6 Caron, S.; Vazquez, E.;Wojcik, J. M. J. Am. Chem. Soc. 2000, 122, 712.   DOI   ScienceOn
7 Soine, W. H. Med. Res. Rev. 1986, 6, 41.   DOI   ScienceOn
8 Itoh, T.; Takagi, Y.;Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61,2158.   DOI   ScienceOn
9 Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J.S. J. Am Chem. Soc. 1994, 116, 2647.   DOI   ScienceOn
10 Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. Am. Chem.Soc. 1982, 104, 7294.   DOI
11 Ruano, J. L. G.; Garcia, M. C.; Castro, A. M. M.; Ramos, J. H. R.Org. Lett. 2002, 4, 55.   DOI   ScienceOn
12 Im, D. S.; Cheong, C. S.; Lee, S. H.; Youn, B. H.; Kim, S. C.Tetrahedron 2000, 56, 1309.   DOI   ScienceOn
13 Weber, H. K.; Stecher, H.; Faber, K. Biotech. Lett. 1995. 17,803.   DOI
14 Fadel, A.; Garcia-Argote, S. Tetrahedron: Asymmetry 1996, 7,1159.   DOI   ScienceOn
15 Kroutil, W.; Kleewein, A.; Faber, K. Tetrahedron: Asymmetry1997, 8, 3251.   DOI   ScienceOn
16 Carnell, A. J.; Hernandez, M. L. E.; Pettman, A.; Bickley, J. F.Tetrahedron Lett. 2000, 41, 6929.   DOI   ScienceOn