Studies on N-Activation for the Lipase-Catalyzed Enantioselective Preparation of β-Amino Esters from 4-Phenylazetidin-2-one.
- Resource Type
- Article
- Authors
- Sundell, Riku; Kanerva, Liisa T.
- Source
- European Journal of Organic Chemistry. Mar2015, Vol. 2015 Issue 7, p1500-1506. 7p.
- Subject
- *BIOCATALYSIS
*ENANTIOSELECTIVE catalysis
*ENZYMES
*LACTAMS
*SOLVOLYSIS
*LIPASES
- Language
- ISSN
- 1434-193X
The effect of N-substitution was examined for the enantioselective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparative-scale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl ( R)-3-amino-3-phenylpropanoates with enantiomeric excess ( ee) values >99 % in up to a 49 % isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl ( S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction. [ABSTRACT FROM AUTHOR]