Lipase-catalyzed optical resolution of trifluoro(aryl) ethanols

Citation
K. Kato et al., Lipase-catalyzed optical resolution of trifluoro(aryl) ethanols, J MOL CAT B, 11(4-6), 2001, pp. 287-294
Citations number
23
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
ISSN journal
1381-1177 → ACNP
Volume
11
Issue
4-6
Year of publication
2001
Pages
287 - 294
Database
ISI
SICI code
1381-1177(20010122)11:4-6<287:LOROTE>2.0.ZU;2-M
Abstract
Optical resolutions of racemic 2,2,2-trifluoro-1-(aryl)ethanols - (l-naphth yl), (2-naphthyl), (4-methylnaphthyl), (phenyl), (1-pyrenyl) - were achieve d by lipase-catalyzed enantioselective acetylations with vinyl acetate as a n acetyl donor in octane, and (S)-acetates and (R)-alcohols were obtained. Among the Lipases tested, lipase from Pseudomonas aeruginosa (Lipase LIP, T oyobo) showed good enantioselectivity for above ethanols. However, no acety lation occurred with sterically hindered alcohols - (9-phenanthryl), (9-ant hryl), (2-methylnaphthyl), (2, 4, 6-trimethylphenyl) - by various Lipases. The resolutions of the three alcohols were carried out by the enantioselect ive alcoholysis or hydrolysis of their chloroacetates by lipase LIP. (C) 20 01 Elsevier Science B.V. All rights reserved.