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Enzymatic resolution of 2,2,2-trifluoro-1-arylethylamine derivatives by Pseudomonas fluorescens lipase in organic solvents

Authors :
Takao Saito
Katsuya Kato
Yoshiyuki Yokogawa
Yuefa Gong
Source :
Journal of Molecular Catalysis B: Enzymatic. 30:61-68
Publication Year :
2004
Publisher :
Elsevier BV, 2004.

Abstract

Amination of phenyl trifluoromethyl ketone with ammonium formate (Leuckart-Wallach reaction) in a one-pot reaction gave 2,2,2-trifluoro-1-phenylethylamine (3a) in high yield (81%). Other fluorinated 1-arylethylamine derivatives were obtained from their corresponding aryl ketones in moderate to good yields (55–81%). Enzymatic resolution of racemic 3a was done with Pseudomonas fluorescens lipase (Amano lipase AK) via enantioselective alcoholysis of its chloroacetamide (4a) with n-amyl alcohol in diisopropyl ether giving good enantioselectivity (E-value = 44). Other amines also were resolved by lipase AK under similar conditions (E-values = 25 to >100).

Details

ISSN :
13811177
Volume :
30
Database :
OpenAIRE
Journal :
Journal of Molecular Catalysis B: Enzymatic
Accession number :
edsair.doi...........408712e3ed2e0c3ac356cb5135459788
Full Text :
https://doi.org/10.1016/j.molcatb.2004.03.006