title: Straightforward preparation of biologically active 1-aryl- and 1-heteroarylpropan-2-amines in enantioenriched form.
abstract: Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparation of the corresponding enantioenriched (R)-amides and (S)-amines by aminolysis reactions. Likewise, dynamic kinetic resolutions (DKR) have been successfully achieved combining the use of CAL-B and Shvo's catalyst. This research constitutes the first example of a lipase-catalyzed DKR process of β-substituted isopropylamines.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006, Oviedo, Spain.
authors.forename: María
authors.initials: M
authors.lastname: Rodríguez-Mata
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor-Fernández
authors.forename: Javier
authors.initials: J
authors.lastname: González-Sabín
authors.forename: Francisca
authors.initials: F
authors.lastname: Rebolledo
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: D000588:Amines / Q000737:chemistry* / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D005656:Fungal Proteins; D008049:Lipase; C431349:lipase B, Candida antarctica; D011407:Propane