徐华栋老师课题组在Angewandte Chemie, International Edition发表研究论文

发布时间:2014-07-14浏览次数:715

Copper-Catalyzed Cyclization/aza-Claisen Rearrangement Cascade Initiated by Ketenimine Formation: An Efficient Stereocontrolled Synthesis of α-Allyl Cyclic Amidines

Dr. Hua-Dong Xu, Zhi-Hong Jia, Ke Xu, Mei Han, Sai-Nan Jiang, Jing Cao, Jia-Cheng Wang and Dr. Mei-Hua Shen

Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201405331

 

Abstract: An efficient and convenient synthesis of α-allyl cyclic amidines has been achieved by applying a novel cascade reaction. Copper(I)-mediated in situ N-sulfonyl ketenimine formation from the reaction of a terminal alkyne with sulfonyl azide is followed by an intramolecular nucleophilic attack on the central carbon atom by an allylic tertiary amine, and then an aza-Claisen rearrangement takes place through a chair transition state to furnish the titled amidines with complete stereocontrol.