Application Of Proline Derivatives In Asymmetric Aldol Reaction And Synthesis Of 3-hydroxylindole Derivatives

Isatin(Isatin) is a naturally occurring oxidized indole derivative, a widely occurring structural unit in many natural products. Isatin and its derivatives display rich biological activity, the development of the Isatin derivatives in pharmaceutical chemistry has become one of the hot research topic in recent years.In this thesis, a new method for synthesis of substituted C3-hydroxyl isatin derivatives is developed. In addition, proline derivatives as organic molecule catalysts were synthesized and used in the asymmetric Aldol reaction of benzaldehyde derivatives and ketones.In the first part, the reaction of p-nitro benzaldehyde with cyclohexanone was chose as the model reaction. Various reaction conditions including catalysts, amount of catalysts were optimized. Results show that withdrawing groups such as nitro are beneficial to the reaction, and good yields and stereoselectivity of corresponding products(up to 99% ee) were obtained, however, other substituents such as F-, Cl-etc groups have no apparent reactivity towards corresponding products.In the second part, a new kind of 3-hydroxy indolone derivatives were synthesized by the reaction of Benzylisatin derivatives with nitro propyl methy lsulfonate in the presence of PTC, n-Bu4 NBr. These 3-hydroxy indolone compounds, which have potential applications in biological and medical fields, were synthesized in good to excellent yields(up to 99% yield), and their structures were characterized and identified by 1H NMR, 13 C NMR and X-Ray single crystal diffraction.