手性奎宁季铵盐配体的制备及在Darzens反应中的催化作用研究  

Research on Synthesis of Chiral Quinine Quaternary Ammonium Ligand and Its Catalyzing Activity for Darzens Reaction

作　　者：何健兴[1] 苏晶[1] 林汉森[1] 李建组[1] 

机构地区：[1]广东药学院药科学院,广东广州510006

出　　处：《广东化工》2013年第7期27-29,31,共4页Guangdong Chemical Industry

摘　　要：文章以奎宁碱为母体,利用一系列卤代烃与奎宁碱发生季铵化反应,生成一系列手性奎宁季铵盐配体,所合成的配体结构均经1H-NMR、IR、MS确证。并考察了该系列催化剂在不对称相转移催化2-氯代苯乙酮和苯甲醛的Darzens缩合反应中的催化性能,发现其手性催化性能跟取代基的立体位阻及电负性大小有关,其中由2-氟-4-溴苄基与奎宁形成的手性季铵盐不对称催化效果最好,所得缩合产物的ee值最高为46%。Through using a series of halogenated hydrocarbons and quinine alkaline quaternization reaction,a series of chiral quinine quaternary ammonium salt ligand were generated with quinine as base matrix and its synthesized ligand structure were confirmed by 1H-NMR,IR,MS.And catalytic performance of ligands in Darzens condensation reaction between 2-chloroacetophenone and benzaldehyde in the asymmetric catalytic condition was investigated,implying that the chiral catalytic properties were associated with the steric size of substituents.And the best enantioselectivity for 46 %was obtained.

关 键 词：手性奎宁季铵盐 配体 不对称相转移催化 Darzens反应 

分 类 号：TQ251.2[化学工程—有机化工]