Theoretical study of stereoselectivity for syn-selective cross-aldol reactions of aldehydes catalyzed by chiral diamine organocatalysts

摘要：

　　Quantum mechanical calculations have been performed to study the stereoselectivities in the direct cross-aldol reactions of aldehydes catalyzed by simple chiral diamines.The detailed computational studies on the stereochemistry-controlling step of the subject reactions have been presented by DFT calculations at the B3LYP/6-31G* level.The poor agreement between the calculated and the observed diastereomeric ratio and enantiomeric excess values is obtained for all diamines catalysts.Further M06-2X calculations can provide a reasonable explanation for the observed syn-selectivities of the asymmetric cross-aldol reaction between propionaldehyde and 4-nitrobenzaldehyde.

关键词： Organocatalysis Syn-aldol Diamine Stereoselectivity DFT

作者: Chengyan Zhao Aiping Fu Hongliang Li Ping Wang Yong Xu Yunbo Duan

作者单位: Institute for Computational Science and Engineering, Laboratory of New Fiber Materials and Modern Textile,the Growing Base for State Key Laboratory, Qingdao University, Qingdao 266071, China

会议类型: 国际会议

会议名称: 2013 International Conference on Computational Science and Engineering(2013年计算科学与工程国际学术研讨会)

会议地点: 青岛

会议语种:英文

页码: 356-362

在线出版日期: 2013-07-01（万方平台首次上网日期，不代表论文的发表时间）