一种新型C(2)对称手性催化剂的合成及其在催化前手性酮的不对称硼烷还原反应中的应用。
Synthesis of a new C(2)-symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones.
作者信息
Zhou Yan, Wang Wen-Hua, Dou Wei, Tang Xiao-Liang, Liu Wei-Sheng
机构信息
College of Chemistry and Chemical Engineering, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
出版信息
Chirality. 2008 Feb;20(2):110-4. doi: 10.1002/chir.20503.
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.
通过2,5-二氯甲基-1,3,4-恶二唑与(S)-α,α-二苯基-2-吡咯烷甲醇反应，成功合成了一种新型的C(2)-对称手性催化剂3,5-双[(2S)-(羟基-二苯基甲基)-吡咯烷-1-基甲基]-1,3,4-恶二唑，并将其应用于硼烷催化前手性酮的不对称还原反应。当催化剂负载量为1 mol%时，在芳香族酮和α-卤代酮的还原反应中分别观察到高达86.8%和94.5%的对映体过量。
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