Preparation of highly optically pure homochiral sulfide-containing alcohols via oxazaborolidine-catalyzed asymmetric borane reduction of ketones.
Highly optically pure homochiral 1-(4-alkylthiophenyl) alcohols were prepared efficiently and practically via the oxazaborolidine-catalyzed asymmetric borane reduction of prochiral ketones in toluene at 25 degrees C. The coordination of the sulfur atom in the ketones to the boron atom in the catalyst and borane can be inhibited under these reduction conditions.
Xu
Jiaxi
J
Deparment of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing, P R China. jia_xu_99@yahoo.com
Wei
Tiezheng
T
Xia
Jiakun
J
Zhang
Qihan
Q
Wu
Hesong
H
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*; D013696:Temperature
D000438:Alcohols; D001880:Boranes; D001896:Boron Compounds; D007659:Ketones; D013440:Sulfides; D001895:Boron