Synthesis of a new C(2)-symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones.
A new C(2)-symmetric chiral catalyst 3,5-bis[(2S)-(hydroxy-diphenylmethyl)- pyrrolidin-1-ylmethyl]-1,3,4-oxadiazole was successfully synthesized by the reaction of 2,5-dichloromethyl-1,3,4-oxadiazole with (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol, and applied to the catalytic asymmetric reduction of prochiral ketones with borane. When the catalyst loading was 1 mol %, enantiomeric excesses of up to 86.8% and 94.5% were observed in reduction of aromatic and alpha-halo ketones, respectively.
Zhou
Yan
Y
College of Chemistry and Chemical Engineering, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Wang
Wen-Hua
WH
Dou
Wei
W
Tang
Xiao-Liang
XL
Liu
Wei-Sheng
WS