(3-氮-吗啉)-1-(4-氯)-苯基-1-丙酮不对称还原产物光学活性的理论计算

Theoretical Computation on Optical Activity of Enantioselective Reduction Product of 1-(4-Chloro-phenyl) -3-morpholin-4-yl-propane-1-one

采用AM1方法对(S)-4-苄基-5,5-二苯基-1,3,2-噁唑硼烷催化(3-氮-吗啉)-1-(4-氯)-苯基-1-丙酮不对称还原反应的立体控制步骤进行了计算,获得了R和S型过渡态的优化构型及其热焓和熵等热力学参数,计算得到了该步反应中生成R和S型对映体的反应速率常数之比,据此得到的不对称还原反应最终产物的光学活性e.e.的理论计算值,与实验结果相近.

AM1 method was performed to study the stereo-controlling step of the enantioselective reduction of 1-(4-chloro-phenyl)-3-morpholin-4-yl-propane-1-one catalyzed by (S)-4-benzyl-5,5-diphenyl- 1,3,2-oxazaborolidine. The optimized geometries, thermal enthalpies and entropies of the (R)- and (S)- transition states in this step were obtained. The calculated optical activity (e.e. value) of the final product was in good agreement with the experimental result.