手性磺酰胺的合成及在苯乙酮的不对称氢转移反应中的应用  

Synthesis of chiral sulfonamides and their application in asymmetric transfer hydrongenation of acetophenone

作　　者：周忠强[1] 武利华[1] 刘洋[1] 

机构地区：[1]中南民族大学化学与材料科学学院,湖北武汉430074

出　　处：《化学试剂》2008年第10期729-730,733,共3页Chemical Reagents

基　　金：湖北省自然科学基金资助课题(2007ABA291)

摘　　要：以辛可宁为原料,经Mitsunobu反应合成了9-氨基(9-脱氧)表辛可宁,然后分别与8-喹啉磺酰氯、苯磺酰氯、对甲基苯磺酰氯、对氯苯磺酰氯反应,合成了4个手性磺酰胺化合物。对这些磺酰胺在苯乙酮的不对称氢转移反应中的催化性能进行了考察,在80℃下反应,当n(苯乙酮)∶n(手性磺酰胺Ru(Ⅱ)配合物)∶n(氢氧化钾)=50∶1∶2.5时,获得的最大转化率为96.0%。9-Amino（9-deoxy）epicinchonine was synthesized from cinchonine through the Mitsunobu reaction followed by treating with 8-quinolinesulfonyl chloride,benzenesulfonyl chloride,p-toluenesulfonyl chloride,4chlorobenzenesulfonyl chloride,respectively,to give four chiral sulfonamides.These sulfonamides were used as ligands in asymmetric transfer hydrongenation of acetophenone.When the reaction was carried out using a feed rate of acetophenone∶chiral sulfonamide Ru（Ⅱ） complex∶KOH（molar ratio）=50∶1∶2.5 at 80 ℃,a maximum 96.0% conversion was obtained.

关 键 词：辛可宁 磺酰胺 合成 不对称氢转移 

分 类 号：O621.3[理学—有机化学]