Copper ion-induced activation and asymmetric benzoylation of 1,2-diols: kinetic chiral molecular recognition.
New catalytic ability of copper(II) ion has been exploited for monobenzoylation of 1,2-diols. The catalyst can be readily modified by ligation to acquire higher stereoselectivity. Highly effective kinetic resolution of dl-1,2-diols was achieved. The enantiodiscrimination process was clearly shown to be controlled by the kinetics of acylation of dl-1,2-diols. The catalytic method was successfully applied to asymmetric desymmetrization of meso-hydrobenzoin.
Matsumura
Yoshihiro
Y
Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. matumura@net.nagasaki-u.ac.jp
Maki
Toshihide
T
Murakami
Sachie
S
Onomura
Osamu
O
D000438:Alcohols / Q000737:chemistry*; D001573:Benzoin / Q000031:analogs & derivatives / Q000737:chemistry; D001592:Benzyl Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D007700:Kinetics; D013237:Stereoisomerism
D000438:Alcohols; D001592:Benzyl Alcohols; D003300:Copper; D001573:Benzoin