Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex.
The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl(2)(PPh(3))(3) with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities.
Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, kita 13, nishi 8, Sapporo 060-8628, Japan. yasuyama@eng.hokudai.ac.jp
Yasunori
Y
Yamamoto
Tomohiko
T
Shirai
Norio
N
Miyaura
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D006038:Glyoxylates / Q000138:chemical synthesis / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D056831:Coordination Complexes; D006038:Glyoxylates; D012428:Ruthenium