title: Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester.
abstract: Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/kslow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only induced the enantioselectivity but also promoted protolactonization.
authors.affiliation: Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Sakuma
authors.forename: Akira
authors.initials: A
authors.lastname: Sakakura
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D017976:Phosphorus Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D007783:Lactones; D017976:Phosphorus Acids