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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (07): 822-825. 上一篇    下一篇

研究论文

苯甲醛不对称烯丙基化反应研究

陈万锁*，陈志荣   

  1. (浙江大学化工系联合反应工程研究所 杭州 310027)
  • 收稿日期:2004-08-23 修回日期:2005-01-24 发布日期:2005-06-30
  • 通讯作者: 陈万锁

Quantum Chemical Study on Asymmetric Allylation of Benzaldehyde

CHEN Wan-Suo*,CHEN Zhi-Rong   

  1. (Department of Chemical Engineering, Zhejiang University, Hangzhou 310027)
  • Received:2004-08-23 Revised:2005-01-24 Published:2005-06-30
  • Contact: CHEN Wan-Suo

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1939

被引次数

3

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.

关键词: 苯甲醛, 不对称烯丙基化反应, 密度泛函理论

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 prod-uct predicted was in agreement with the experiment.

Key words: benzaldehyde, density functional theory, asymmetric allylation