噁唑硼烷对苯甲酮不对称还原反应催化性能的理论计算  

Theoretical Study on Enantioselectivity of Oxazaborolidine Catalysts for Reduction of Phenyl Methyl Ketone

作　　者：樊建芬[1] 黄洁[1] 卢运祥[1] 孙云鹏[1] 

机构地区：[1]苏州大学化学系,江苏苏州215006

出　　处：《化学研究》2005年第3期58-61,共4页Chemical Research

基　　金：苏州大学君政基金课题

摘　　要：采用AM1方法研究了四种1,3,2-噁唑硼烷催化剂对苯甲酮不对称还原反应的催化性能,计算了立体控制步骤中生成R和S型催化配合物的反应热和活化能,并根据立体控制步骤中R和S型过渡态的熵和焓等参数,计算了四种催化反应体系最终产物的绝对构型及光学活性(e.e.%),据此对四种催化剂的对映选择性作出了评价.The AM1-SCF MO method has been applied to study the enantioselectivities of four kinds of 1,3, 2-oxazaborolidine as the catalysts in the reduction of phenyl methyl ketone. The optimized geometries, thermal anthalpies and entropies of R and S transition states in the stereo-controlling steps of the four catalyzed-reductions have been obtained. The absolute configurations and optical activities （e. e. % values） of the final products are calculated. It was found that （S） -3-methyl-4-benzyl-5, 5-diphenyl-1,3, 2-oxazaborolidine shows better enantioselectity in the catalysts.

关 键 词：AM1 苯甲酮 不对称还原反应 对映选择性 嗯唑硼烷催化剂 

分 类 号：O641.12[理学—物理化学]