First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol
Paweł Borowiecki , Sylwia Balter , Iwona Justyniak , Zbigniew Ochal
AbstractA 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.
|Journal series||Tetrahedron-Asymmetry, ISSN 0957-4166|
|Publication size in sheets||0.5|
|ASJC Classification||; ; ;|
|Score|| = 25.0, 02-02-2020, ArticleFromJournal|
= 25.0, 02-02-2020, ArticleFromJournal
|Publication indicators||= 6; = 5; : 2013 = 0.716; : 2013 = 2.165 (2) - 2013=2.097 (5)|
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