脯氨醇硅醚催化合成手性苯并吡喃的影响因素研究

The Influencing Factors on the Synthesis of Chiral Benzopyran Catalyzed by Prolinol Silyl Ether

利用水杨醛与肉桂醛的氧杂迈克尔加成/羟醛缩合反应合成手性苯并吡喃,并对影响反应的因素进行考察,比较了溶剂、有机小分子酸、有机小分子碱、有机小分子酸碱混合使用、硅基Lewis酸和水杨醛与肉桂醛的物质的量之比对反应的影响.结果表明,当以脯氨醇硅醚为催化剂,二氯甲烷为溶剂,4-氯苯甲酸为添加剂,n(水杨醛)∶n(肉桂醛)=2∶1时,反应可以达到93%的产率和83%的ee值.

The experiment synthesized chiral benzopyran with the domino oxa-Michael/aldol reaction of salicyladehyde and cinnamaldehyde, investigated the factors influenced the reaction, and compared the effects of the ratios of solvent, small organic molecule acids, small organic molecule bases, the mixed use of small organic molecule acids together with bases, silyl Lewis acids and molar ratio of salicylaldehyde to cinnamaldehyde on the reaction. The results show that with prolinol silyl ether as organocatalyst, dichloromethane as solvent, 4-chlorobenzoic acid as addictive, and the molar ratio of salicylaldehyde to einnamaldehyde is 2：1, the yield can achieve 93%, and the excellent enantioselectivity can be 83M.