Carbonate can be formed by the reaction of ethylene oxide with carbon dioxide. The efficient use of carbonate can promote the chemical conversion of carbon dioxide, which is one of the potential petroleum carbon source substitutes. It has important strategic significance. Recently, the Journal of Chinese Journal of Science and Technology interviewed Xi'an. Guo Wusheng, a professor at the Institute of Frontier Science and Technology at Jiaotong University, learned that he used carbonates and their derivatives as raw materials to achieve a series of challenging synthesis of drug molecules and intermediates, and to expand the chemistry of carbonates and derivatives. 4. Application, promoted the stereoselective synthesis of polysubstituted olefins and the development of allyl chemistry.
Allylamine is a very important basic unit in synthetic chemistry and medicinal chemistry. Allyl nucleophilic substitution is the most commonly used method for the synthesis of allylamine. Guo Wusheng told reporters how to use allylic chemistry to efficiently construct important pharmaceutical intermediate chirality. A-disubstituted allylamine has great challenges. At the same time, for palladium-catalyzed allylic nucleophilic substitution reaction, amines are more likely to attack the allyl palladium terminal carbon with less steric hindrance to form linear products, how to guide the amine attack position. The larger allyl palladium meta-carbon is the key to the synthesis of chiral a-disubstituted allylamine branched products.
Therefore, Guo Wusheng led the team to successfully realize the asymmetric synthesis of a-disubstituted allylamine by using cyclic, linear carbonate as raw material and hydrogen bond induction strategy. Phenol is also suitable for the synthesis of chiral allyl groups in this system. Aromatic ether. The study of allyl aromatic amine was selected for JACS in the month of publication. The academician of the American Academy of Sciences, Hisashi Yamamoto, president of the Japanese Chemical Society, twice introduced this series of work as a recent research highlight, and concluded that the synthesis of a-disubstituted allylamine is ' Quite challenging, and pointed out that Guo Wusheng realized the synthesis of a-disubstituted allylamine with a 'very simple new method'.
Multi-substituted olefin fragments are another basic unit widely found in natural products and drug molecules. How to construct a single stereo configuration, stereoselective synthesis of polysubstituted olefins is a key scientific problem in this type of research. As a class of olefins Allyl alcohol is an important chemical raw material for the synthesis of glycerol, butanediol, plasticizers and engineering plastics. Studying the stereoselective synthesis of new substituted allyl alcohol skeletons can not only promote its new application in industrial production, but also It also provides reference for the stereocontrolled synthesis of multi-substituted olefins.
Guo Wusheng uses allyl cyclic carbonate as raw material to catalyze the decarboxylation to form a six-membered palladium intermediate. It inhibits the formation of stereoisomer by-products and realizes stereoselective synthesis of polysubstituted allyl alcohol or amine. The study was selected as the cover of the JACS cover, which is considered to be a sophisticated tool for total synthesis, which is applicable to different nucleophiles including water, and has a stereoselective synthesis of polysubstituted allyl alcohols. Strong universality will promote the development of stereoselective synthesis of polysubstituted olefins.
At the same time, Guo Wusheng also observed that urethane compounds have important applications in pesticides and medicine, and can also be used as monomers for synthetic polyurethanes. The global production of synthetic polyurethanes reached 18 million tons in 2017. Cyclic carbonate amines Is the best way to synthesize urethane and no waste. However, the nucleophilicity of aromatic amines is poor. How to achieve aromatic amination of cyclic carbonates to form urethane is not solved. The key scientific problem. Through research, Guo Wusheng has synthesized chiral g-disubstituted amino acids, cis and trans urethane and its derivatives, and synthesized the treatment of T cell lymphoma drug Vorinostat, muscle relaxant Carisoprodol, a drug molecule such as the Felbatol derivative of the epilepsy treatment.