title: Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen-Mn(III) complexes.
abstract: Three new chiral salen-Mn(III) complexes with sugars at the C-5(5') positions of the salicylaldehyde moieties of the salen ligand were synthesized. Their structures were characterized by FTIR, MS, and elemental analysis. The complexes together with two previously reported ones were successfully used as chiral catalysts for the oxidative kinetic resolution (OKR) of 1-phenylethanol using PhI(OAc)2 as an oxidant and KBr as an additive. Excellent enantiomeric excess (up to 89%) of the product was achieved in 0.5h at 20 degrees C. The results showed that the sugars at C-5(5') of salicylaldehyde moieties in the ligand had influences on the catalytic performances of the complexes. It was concluded that the sugars with the same rotation direction of polarized light as the diimine bridge within the complex could enhance the chiral induction of the complex in the OKR of 1-phenylethanol, but the sugars with the opposite one would reduce that of the corresponding complex.
authors.affiliation: School of Chemical Engineering, Hebei University of Technology, Tianjin 300130, PR China.
authors.forename: Furong
authors.initials: F
authors.lastname: Han
authors.forename: Jiquan
authors.initials: J
authors.lastname: Zhao
authors.forename: Yuecheng
authors.initials: Y
authors.lastname: Zhang
authors.forename: Weiyu
authors.initials: W
authors.lastname: Wang
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Zuo
authors.forename: Junwei
authors.initials: J
authors.lastname: An
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry*; D007700:Kinetics; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010626:Phenylethyl Alcohol / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000447:Aldehydes; D005029:Ethylenediamines; C013243:salicylaldehyde; D008345:Manganese; C011452:disalicylaldehyde ethylenediamine; D010626:Phenylethyl Alcohol