苯甲醛不对称烯丙基化反应研究  

Quantum Chemical Study on Asymmetric Allylation of Benzaldehyde

作　　者：陈万锁[1] 陈志荣[1] 

机构地区：[1]浙江大学化工系联合反应工程研究所,杭州310027

出　　处：《有机化学》2005年第7期822-825,i003,共5页Chinese Journal of Organic Chemistry

摘　　要：对D-(-)-酒石酸异丙酯修饰的烯丙基硼试剂与苯甲醛的不对称烯丙基化反应机理进行了研究.反应中间体和过渡态进行B3LYP/6-31G(d,p)全优化,发现主要经六元环椅式过渡态生成手性烯丙基羟基化合物.由相对反应速率理论,预测的主产物构型与实验的R-手性醇相吻合.The quantum chemical method was employed to study the modified asymmetric allylation of benzaldehyde controlled by diisopropyl D-(-)-tartrate auxiliary. All the structures were optimized completely at the B3LYP/6-31G(d,p) level. The (R)-secondary alcohol could be achieved mainly through a six-membered ring chair-like transition state structure. From the relative reaction rate theory the main product predicted was in agreement with the experiment.

关 键 词：烯丙基化 不对称 苯甲醛 反应研究 B3LYP 反应中间体 羟基化合物 反应机理 反应速率 过渡态 异丙酯 酒石酸 六元环 手性醇 椅式 构型 硼 

分 类 号：O621.25[理学—有机化学]