手性三齿Schiff-base配体的合成及其催化的不对称Henry反应研究  

Synthesis of chiral tridentate schiff-base ligands and their catalytic research for asymmetric Henry reaction

作　　者：宋庆宝[1] 夏婷[1] 安晓霞[1] 

机构地区：[1]浙江工业大学化学工程与材料学院,浙江杭州310032

出　　处：《浙江工业大学学报》2014年第1期73-76,共4页Journal of Zhejiang University of Technology

基　　金：浙江省自然科学基金资助项目(LY12B02016)

摘　　要：以L-酪氨酸甲酯盐酸盐为原料,通过格氏反应合成了一种手性β-氨基醇;以水杨醛为原料,通过溴代反应合成了3,5-二溴水杨醛和5-溴水杨醛;将手性β-氨基醇和溴代水杨醛在乙醇中缩合,制备了两种手性三齿Schiff-base配体.产物的结构经IR,1 H NMR,13C NMR和MS表征确定.将配体应用于催化不对称Henry反应中,考察其在不同反应条件下的催化性能,在最优化的反应条件下,不同底物均获得了较好的催化效果,产率最高达95%,ee值最高达90%.A β-amino alcohol was prepared from L-tyrosine methyl ester hydrochloride through Grignard reaction.3,5-dibromosalicylaldehyd and 5-bromosalicylaldehyde were prepared from salicylaldehyde through bromination reaction.They were condensed in ethanol to give two kinds of chiral tridentate Schiff-base ligands.The structures of these ligands were confirmed by IR,1H NMR,13C NMR and MS.The ligands were applied in catalytic asymmetric Henry reactions.Different reaction conditions were tested in this process.Under the optimal conditions,different arylaldehydes gained better catalytic effects with good yields （up to 95％） and high enantioselectivities（up to 90％）.

关 键 词：不对称催化 Β-氨基醇 溴代水杨醛 SCHIFF-BASE Henry反应 

分 类 号：TQ246.3[化学工程—有机化工]