Study On The Reaction Of Aryl Grignard Reagents With Vinyl Acetate

1,3-diol unit usually existed in some natural products, and these products contain1,3-diol unit often have diverse biological activities. For it’s so common that the1,3-diolexisted in the natural products, the research on constructing the structure contain1,3-unitattracted much attention of chemists and biologists. Although these multi-alcohol chainsseem simple, but it’s very difficult to synthesis, determinate, and separate for the chiralcenters contained in the products. So it’s of important significance for seeking a method ofhigh stereoselectivity in the product synthesis.The Grignard reagent is a very important chemical reagent, and widely used inorganic synthesis. Recently, our group synthesized series of symmetrical1,3-diols throughthe react of aryl Grignard reagent with isoproenyl acetate. On the basis of the previouswork, we take further studies of the reaction of aryl Grignard reagent with vinyl acetate.11asymmetric1,3-diol were obtained and anti-and syn-1,3-p-tolylbutane-1,3-diol weresuccessfully separated. All the products were confirmed by¹H NMR,¹³C NMR, IR,ESI-MS. The single crystal of product2and6were obtained from slow evaporation of itspetroleum ether-ethyl acetate （5:1） solution at room temperature, X-Ray diffractionanalysis were performed. The possible mechanism of the reaction was studied.