First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol
Publication type: Journal Article
Publication date: 2013-09-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A simple chemoenzymatic synthesis of 1-(9 H -fluoren-9-yl)ethanol stereoisomers is described. The enantiomers were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of commercially available lipases. High-throughput screening and subsequent exhaustive investigation of the utility of the lipases in a stereoselective process of introducing chirality have been carried out. Lipase A from Candida antarctica as a cross-linked aggregate (CAL-A-CLEA) was the most efficient enzyme for the resolution of the title compound providing ( S )-1-(9 H -fluoren-9-yl)ethanol and its ( R )-acetate in enantiopure form (>99% ee). Under mild reaction conditions, excellent enantioselectivity ( E = 407), and good isolated yields of the products were obtained.
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Borowiecki P. et al. First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol // Tetrahedron Asymmetry. 2013. Vol. 24. No. 18. pp. 1120-1126.
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Borowiecki P., Balter S., Justyniak I., Ochal Z. First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol // Tetrahedron Asymmetry. 2013. Vol. 24. No. 18. pp. 1120-1126.
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TY - JOUR
DO - 10.1016/j.tetasy.2013.07.005
UR - https://doi.org/10.1016/j.tetasy.2013.07.005
TI - First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol
T2 - Tetrahedron Asymmetry
AU - Borowiecki, Paweł
AU - Balter, Sylwia
AU - Justyniak, Iwona
AU - Ochal, Zbigniew
PY - 2013
DA - 2013/09/01
PB - Elsevier
SP - 1120-1126
IS - 18
VL - 24
SN - 0957-4166
SN - 1362-511X
ER -
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@article{2013_Borowiecki,
author = {Paweł Borowiecki and Sylwia Balter and Iwona Justyniak and Zbigniew Ochal},
title = {First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol},
journal = {Tetrahedron Asymmetry},
year = {2013},
volume = {24},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tetasy.2013.07.005},
number = {18},
pages = {1120--1126},
doi = {10.1016/j.tetasy.2013.07.005}
}
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MLA
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Borowiecki, Paweł, et al. “First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol.” Tetrahedron Asymmetry, vol. 24, no. 18, Sep. 2013, pp. 1120-1126. https://doi.org/10.1016/j.tetasy.2013.07.005.