Chin. J. Org. Chem. ›› 2003, Vol. 23 ›› Issue (12): 1400-1406. Previous Articles     Next Articles

取代基对手性唑噁唑硼烷催化还原苯基乙基酮对映体选择性影响的理论研究

杨思娅;孙成科;林雪飞   

  1. 曲靖师范学院化学系
  • 发布日期:2003-12-25

Theoretical Study on the Influence of Substituents on Enantioselecthity in Branched-Oxazaborolidine-Catalyzed Reductions of Phenyl-ethyl Ketone

Yang Siya;Sun Chengke;Lin Xuefei   

  1. Department of Chemistry,Qujing Normal College
  • Published:2003-12-25

The influence of substituents on the enantioselectivity in asymmetric branched-oxazaborolidine-catalyzed reductions of phenyl- ethyl ketone has been studied by using AMI MO method and transition state theory. The results show that the enantioselectivity is determined by the ratio of the rate constants of two parallel reactions conducting to spatial configurations (R) and (S). When the substituents connecting with C(4) and C(5) are in cis-form the reduction products of phenyl-ethyl ketone in the reactions are mainly of configuration ( R). In asymmetric boron-catalyzed reduction reactions the higher or lower magnitude for enantioselectivity and reaction barrier are governed by various substituents connecting with atoms of oxazaborolidine ring. The computational results are in consistence with experiments.

Key words: TRANSITION STATE THEORY;phenyl-ethyl ketone;oxazaborolidine, ENANTIOMORPH;SELECTIVITY

CLC Number: