title: Kinetic resolution of α-methylene-β-hydroxy esters catalyzed by acyl transfer catalyst An-PIQ.
abstract: A highly efficient nonenzymatic kinetic resolution of a series of structurally diverse racemic α-methylene-β-hydroxy esters utilizing the acyl transfer catalyst An-PIQ and propionic anhydride is reported. This procedure provides recovered alcohols with extremely high ee's (up to >99%) in reasonable conversions and excellent selectivity factors (S up to 108). Several synthetically important substrates were resolved in gram-scale reactions, and highly optically pure α-methylene-β-hydroxy esters were obtained with excellent S values and good yields.
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Shan-Shan
authors.initials: SS
authors.lastname: Jiang
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Qin-Chang
authors.initials: QC
authors.lastname: Xu
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Ming-Yu
authors.initials: MY
authors.lastname: Zhu
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Xingxin
authors.initials: X
authors.lastname: Yu
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Wei-Ping
authors.initials: WP
authors.lastname: Deng
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D007700:Kinetics; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*
chemical_list: D000812:Anhydrides; D004952:Esters; D011422:Propionates; C096126:propionic anhydride