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Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

✍ Scribed by Csaba Paizs; Monica Toşa; Viktória Bódai; György Szakács; Ildikó Kmecz; Béla Simándi; Cornelia Majdik; Lajos Novák; Florin-Dan Irimie; László Poppe

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
143 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (E100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanols (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO 2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d.

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