X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .26. 1,5-ELECTROCYCLIZATION AND TANDEM 1,5-ELECTROCYCLIZATION-ALDOL TYPE CONDENSATION PROCESSES IN IMINES

被引:29
作者
GRIGG, R [1 ]
GUNARATNE, HQN [1 ]
HENDERSON, D [1 ]
SRIDHARAN, V [1 ]
机构
[1] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND
关键词
D O I
10.1016/S0040-4020(01)81969-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 1,2- prototropy route and an iminium ion route to vinyl azomethine ylides are described. In both cases the vinyl azomethine ylides undergo 1,5-electrocyclisation to dihydropyrroles. In the former case the 1,5-electrocyclisation is solvent sensitive and competes with a prototropic process giving the imine of an α, β-unsaturated α-amino ester. The mechanism and solvent sensitivity are discussed. In the latter case the dihyd̀ropyrrole reacts further with aldehydes via an aldol type condensation. © 1990.
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页码:1599 / 1610
页数:12
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