Open Access
Open access
Walter de Gruyter
Open Chemistry
,  volume 12 ,  issue 1 ,  pages 25-32

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

F. Faigl 1, 2
, 
Ervin Kovács 3
, 
Dora Balogh 4
, 
Tamás Holczbauer 5
, 
Mátyás Czugler 5
, 
Béla Simándi 6
1
 
2
 
HUNGARIAN ACADEMY OF SCIENCES
3
 
2Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H-1111, Budapest, Hungary | 
4
 
5
 
3Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary | 
6
 
Publication type: Journal Article
Publication date: 2014-01-01
Walter de Gruyter
scimago Q3
wos Q3
SJR: 0.359
CiteScore: 3.9
Impact factor: 1.9
ISSN: 23915420
Materials Chemistry
General Chemistry
Abstract

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.

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Faigl F. et al. Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine // Open Chemistry. 2014. Vol. 12. No. 1. pp. 25-32.
GOST all authors (up to 50) Copy
Faigl F., Kovács E., Balogh D., Holczbauer T., Czugler M., Simándi B. Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine // Open Chemistry. 2014. Vol. 12. No. 1. pp. 25-32.
RIS |
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RIS Copy
TY - JOUR
DO - 10.2478/s11532-013-0347-8
UR - https://doi.org/10.2478/s11532-013-0347-8
TI - Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine
T2 - Open Chemistry
AU - Faigl, F.
AU - Kovács, Ervin
AU - Balogh, Dora
AU - Holczbauer, Tamás
AU - Czugler, Mátyás
AU - Simándi, Béla
PY - 2014
DA - 2014/01/01
PB - Walter de Gruyter
SP - 25-32
IS - 1
VL - 12
SN - 2391-5420
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2014_Faigl,
author = {F. Faigl and Ervin Kovács and Dora Balogh and Tamás Holczbauer and Mátyás Czugler and Béla Simándi},
title = {Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine},
journal = {Open Chemistry},
year = {2014},
volume = {12},
publisher = {Walter de Gruyter},
month = {jan},
url = {https://doi.org/10.2478/s11532-013-0347-8},
number = {1},
pages = {25--32},
doi = {10.2478/s11532-013-0347-8}
}
MLA
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MLA Copy
Faigl, F., et al. “Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine.” Open Chemistry, vol. 12, no. 1, Jan. 2014, pp. 25-32. https://doi.org/10.2478/s11532-013-0347-8.