Theoretical Investigation Of The Stereoselectivity Of Some Diels-Alder Reactions

Content: Diels-Alder Reaction is found by both Germany chemists O. Diels and his assistant, K.Alder, in 1982. The reaction between diene and dienophile with double bonds or tri-bonds became into the hexahydroxy compounds. Because of good regio- and stereoselectivity, Diels-Alder reaction has become an important tool of synthetic chemistry and a significant subject of theoretical study.However, concerning the opinion of the stereoselectivity of the Diels-Alder reaction, there is no uniform method to confirm. In this thesis, we have explored and explained by using four methods the stereoselectivity of the Diels-Alder reaction, which are transition state theory (TST), secondary orbital interaction (SOI), ABEEMσπmodel combination with the maximum hardness principle (MHP) and local hard-soft acid-base principle (Local HSAB), respectively. Compared with these four methods to confirm the stereoselectivity, we made a reasonable explanation by ABEEMσπmodel combination with Local HSAB for all the Diels-Alder reactions. Used this method, the results are in better accord with the experimental results. This kind of the method is more simple and predictive on the stereoselectivity of the Diels-Alder reaction.