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Paper | Special issue | Vol 40, No. 1, 1995, pp.387-399
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S49
Preparation of γ-Heterosubstituted α,β-Hexenolides and Their 1,3-Dipolar Cycloaddition to 2,3,4,5-Tetrahydropyridine 1-Oxide

Félix Busqué, Pau Cid, Pedro de March, Marta Figueredo and Josep Font

*Departament de Química, Universidad Autonoma de Barcelona, 08193 Bellaterra (Barcelona), Spain


This paper describes the preparation of several γ-heterosubstituted α,β-hexenolides and their 1,3-dipolar cycloaddition to 2,3,4,5-tetrahydropyridine 1-oxide. In all these reactions the formed tricyclic cycloadducts arise exclusively from an exo transition state and the antifacial approach of the reactants is preferred.