First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol

Paweł Borowiecki , Sylwia Balter , Iwona Justyniak , Zbigniew Ochal

Abstract

A simple chemoenzymatic synthesis of 1-(9H-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-(9H-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.
Author Paweł Borowiecki (FC / IBC / DDTB)
Paweł Borowiecki,,
- Department Of Drug Technology And Biotechnology
, Sylwia Balter (FC / IBC / DDTB)
Sylwia Balter,,
- Department Of Drug Technology And Biotechnology
, Iwona Justyniak (FC / IBC / DDTB)
Iwona Justyniak,,
- Department Of Drug Technology And Biotechnology
, Zbigniew Ochal (FC / IBC / DDTB)
Zbigniew Ochal,,
- Department Of Drug Technology And Biotechnology
Journal seriesTetrahedron-Asymmetry, ISSN 0957-4166
Issue year2013
Vol24
No18
Pages1120-1126
Publication size in sheets0.5
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry; 1503 Catalysis
DOIDOI:10.1016/j.tetasy.2013.07.005
URL http://www.sciencedirect.com/science/article/pii/S0957416613002942
Languageen angielski
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tetrahedronasymmetry_2013_24_1120.pdf 490.15 KB
Score (nominal)25
Score sourcejournalList
ScoreMinisterial score = 25.0, 02-02-2020, ArticleFromJournal
Ministerial score (2013-2016) = 25.0, 02-02-2020, ArticleFromJournal
Publication indicators Scopus Citations = 6; WoS Citations = 5; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.716; WoS Impact Factor: 2013 = 2.165 (2) - 2013=2.097 (5)
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