Tetrahedron p. 1599 - 1610 (1990)
Update date:2022-08-04
Topics:
Grigg, R.
Gunaratne, H. Q. Nimal
Henderson, Deirdre
Sridharan, Visuvanathar
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 completes with a prototropic process giving the imine of an α,β-unsaturated α-amino ester.The mechanism and solvent sensivity are discussed.In the latter case the dihydropyrrole reacts further with aldehydes via an aldol type condensation.
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