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2014 | 12 | 1 | 25-32
Tytuł artykułu

Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4-phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (−)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (−)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method. [...]
Wydawca

Czasopismo
Rocznik
Tom
12
Numer
1
Strony
25-32
Opis fizyczny
Daty
wydano
2014-01-01
online
2013-10-27
Twórcy
  • Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H-1111, Budapest, Hungary
autor
  • Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Hungary
  • Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary
  • Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary
  • Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, H-1111, Budapest, Hungary
Bibliografia
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  • [10] P. Lin, L. Chang, R.J. DeVita, J.R. Young, R. Eid, X. Tong, S. Zheng, R.G. Ball, N.N. Tsou, G.G. Chicchi, M.M. Kurtz, K.C. Tsao, A. Wheeldon, E.J. Carlson, W. Eng, H.D. Burns, R.J. Hargreaves, S.G. Mills, Bioorg. Med. Chem. Lett. 17, 5191 (2007) http://dx.doi.org/10.1016/j.bmcl.2007.06.085[Crossref]
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  • [13] V. Gotor, I. Alfonso, E. García-Urdiales, Asymmetric Organic Synthesis with Enzymes. (Wiley-VCH, Weinheim, 2008) 150 http://dx.doi.org/10.1002/9783527622481[Crossref]
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-013-0347-8
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