Quantum chemical study on asymmetric catalysis reduction of imine  

作　　者：LI Ming (李明) TIAN Anmin (田安民) 

机构地区：Department of Chemistry, Southwest-China Normal University, Chongqing 400715, China Department of Chemistry, Sichuan University, Chengdu 610064, China

出　　处：《Science China Chemistry》2003年第2期124-131,共8页中国科学（化学英文版）

基　　金：教育部重点科研项目

摘　　要：The quantum chemical method is employed to study the enantioselective reduction of imine with borane catalyzed by chiral oxazaborolidine. All the structures are optimized completely at the B3LYP/6-31G(d) level. The catalysis property of oxazaborolidine is notable. The reduction goes mainly through the formations of the catalyst-borane adduct, the catalyst-borane-imine adduct, and the catalyst-amidoborane adduct and the dissociation of the catalyst-amidoborane adduct with the regeneration of the catalyst. The controlling step for the reduction is the dissociation of the catalyst-amidoborane adduct. The main reduced product predicted theoretically is (R )-sec- ondary amine, which is in agreement with the experiment.The quantum chemical method is employed to study the enantioselective reduction of imine with borane catalyzed by chiral oxazaborolidine. All the structures are optimized completely at the B3LYP/6-31G(d) level. The catalysis property of oxazaborolidine is notable. The reduction goes mainly through the formations of the catalyst-borane adduct, the catalyst-borane-imine adduct, and the catalyst-amidoborane adduct and the dissociation of the catalyst-amidoborane adduct with the regeneration of the catalyst. The controlling step for the reduction is the dissociation of the catalyst-amidoborane adduct. The main reduced product predicted theoretically is (R)-secondary amine, which is in agreement with the experiment.

关 键 词：CHIRAL oxazaborolidine  imine  ASYMMETRIC CATALYSIS reduction  DFT. 

分 类 号：O6[理学—化学]