title: Kinetic resolution of racemic mandelic acid esters by N,N'-dioxide-scandium-complex-catalyzed enantiomer-selective acylation.
abstract: A simple and efficient acylative kinetic resolution of racemic mandelic acid esters was accomplished with a chiral N,N'-dioxide-scandium(III) complex under mild and base-free reaction conditions. A variety of mandelic acid esters performed well in the reaction, obtaining both acylated products (up to 49% yield, 97% ee) and recovered substrates (up to 49% yield, 95% ee) in high enantioselectivities with perfect selectivity factors (up to 247). The enantioselective recognition and catalytic models were also proposed for the catalytic KR reaction.
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P.R. China), Fax: (+86) 28-8541-8249.
authors.forename: Yuheng
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lin
authors.initials: L
authors.lastname: Zhou
authors.forename: Wangbin
authors.initials: W
authors.lastname: Wu
authors.forename: Tianyu
authors.initials: T
authors.lastname: Huang
authors.forename: Yuting
authors.initials: Y
authors.lastname: Liao
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D004952:Esters; D007700:Kinetics; D008333:Mandelic Acids / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D008333:Mandelic Acids; D009942:Organometallic Compounds; C037938:mandelic acid; D012538:Scandium
keywords: acylation; enantioselectivity; kinetic resolution; mandelic acid esters; scandium