title: Highly diastereo- and enantioselective synthesis of monodifferentiated syn-1,2-diol derivatives through asymmetric transfer hydrogenation via dynamic kinetic resolution.
abstract: The first enantio- and diastereoselective approach to alpha-alkoxy-substituted syn-beta-hydroxyesters through highly efficient catalytic asymmetric transfer hydrogenation via dynamic kinetic resolution reactions from the corresponding racemic beta-ketoesters is described. In this atom-economical process, two contiguous stereogenic centers are generated simultaneously with an excellent diastereoselectivity (up to 99/1) and enantioselectivity (up to 99%), allowing a rapid access to a wide variety of aromatic and heteroaromatic monodifferentiated syn-1,2-diols.
authors.affiliation: Laboratoire Charles Friedel, UMR 7223, ENSCP Chimie ParisTech, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Cartigny
authors.forename: Kurt
authors.initials: K
authors.lastname: Püntener
authors.forename: Tahar
authors.initials: T
authors.lastname: Ayad
authors.forename: Michelangelo
authors.initials: M
authors.lastname: Scalone
authors.forename: Virginie
authors.initials: V
authors.lastname: Ratovelomanana-Vidal
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006865:Hydrogenation; D007700:Kinetics; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004952:Esters; D012428:Ruthenium