Studies On The Method Of Asymmetric Addition Of Benzyl Sulfoxide With Imine And Gold(?) Catalyzed Alkynamide With N,O-acetal

Chirality is a common phenomenon in nature.Different configurations of the same compound have different medicinal effects.Since the well-known "stop reaction event" was reported in 1860's,the chirality control of drug molecules has been widely valued by pharmacists and organic chemists.According to statistics,in the next few years,the proportion of chiral drugs will account for more than 80% of new synthetic drugs.It is one of our important research directions and interests to establish efficient and convenient asymmetric synthesis methods of chiral compounds.Among them,the asymmetric synthesis of nitrogen-containing heterocyclic alkaloids is one of our main research objectives in recent years.This thesis mainly includes the following parts:1.Based on the one pot cascade reaction of imine and Grignard reagent,different chiral benzyl sulfoxide compounds were prepared as by product,and the asymmetric addition methodology between imine and benzyl sulfoxide was established.In this experiment,several o-aminoalcohol skeletons containing chiral sulfoxide were expanded.The products have high diastereoselectivity(dr > 99:1),and the yield is between 45% and 81%.2.Under mild acid conditions,2-73 m,one of the products,was converted into the corresponding trans-4-hydroxy-5-substituted 2-pyrrolidone 2-74 in a yield of 45%.Similarly,trans-5-hydroxy-6-substituted 2-piperidinone compounds can be obtained.3.A new method for the organic synthesis of pyrrole or pyridyloxazinone was established.In this study,pyrrole or pyridyloxazinone compounds were synthesized by the cyclization of alkynamide and N,O-acetal catalyzed by gold(Au).25 products have been developed in the yields between 43% and 93%.The reactions have good substrate adaptability,all products have good diastereoselectivities(dr > 99:1).