An investigation of the scope of the 1,7-electrocyclization of alpha,beta:gamma,delta-conjugated azomethine ylides

作者：Zhang Weimin; Ning Fuqiang; Varadi Linda; Hibbs David E; Platts James A; Nyerges Miklos; Anderson Rosaleen J; Groundwater Paul W^*

来源：Tetrahedron, 2014, 70(22): 3621-3629.

DOI：10.1016/j.tet.2014.03.078

• Azomethine ylides
• 1,5-Electrocyclization
• 1,7-Electrocyclization
• PyrrolinesA azepines

Substituents on the diene component have little influence on the periselectivity of the cyclizations of alpha,beta:gamma,delta-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6 pi) and 1,7-electrocyclization (8 pi) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration.

• 出版日期2014-6-3
• 单位河北医科大学