title: Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst.
abstract: The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.
authors.affiliation: Department of Chemistry-BMC, Uppsala University, Box 576, Uppsala SE-75123, Sweden. albaestrella.diaz@csic.es.
authors.forename: Alba E
authors.initials: AE
authors.lastname: Díaz-Álvarez
authors.affiliation: Department of Chemistry-BMC, Uppsala University, Box 576, Uppsala SE-75123, Sweden. laura.mesas@kemi.uu.se.
authors.forename: Laura
authors.initials: L
authors.lastname: Mesas-Sánchez
authors.affiliation: Department of Chemistry-BMC, Uppsala University, Box 576, Uppsala SE-75123, Sweden. diner@kth.se.
authors.forename: Peter
authors.initials: P
authors.lastname: Dinér
mesh_terms: D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C417980:4-(dimethylamine)pyridine; D004952:Esters; D011725:Pyridines