Abstract: The electronic effect of catalysis and substrates plays an important role in the enantioselectivity of asymmetric catalytic reactions. The stilbenes, especially resveratrol which have a large conjugated system, have satisfactory bioactivities and can take place many reactions. Thus it is valuable to study the structure modification and structure activity relationship. Ten  stilbenes were designed based on the structure of resveratrol, and synthesized through Wittig-Horner reaction in the work. The electron cloud distribution was regulated through changing the type and the position of the substances on benzene ring. The optimized configuration was obtained through calculation under FH/3-21g level.  And the rational mechanism was put forward.  The electronic effect of the substances on the selectivity of catalytic reaction was studied.  In the system, frucase-derived chiral ketone was used to study either the asymmetric epoxidation or oxidation reaction.  As a result, the applied scope of the chiral ketone was determined, the reaction position in the big conjugated system was found when polyoxo-substances exist, the rational analysis of the electronic effect of the substrates was also put forward.

Key words: Stilbene, Electronic effect, Fructose-derived chiral ketone