Highly diastereo- and enantioselective synthesis of monodifferentiated syn-1,2-diol derivatives through asymmetric transfer hydrogenation via dynamic kinetic resolution.
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.
Cartigny
Damien
D
Laboratoire Charles Friedel, UMR 7223, ENSCP Chimie ParisTech, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France.
Püntener
Kurt
K
Ayad
Tahar
T
Scalone
Michelangelo
M
Ratovelomanana-Vidal
Virginie
V
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
D000438:Alcohols; D004952:Esters; D012428:Ruthenium