Cycloaddition reactions of 3,4-dihydro-2H-pyrrole 1-oxide with α,β-unsaturated lactones

David Alonso-Perarnau, Pedro de March, Marta Figueredo, Josep Font, Angeles Soria

Research output: Contribution to journalArticleResearchpeer-review

34 Citations (Scopus)

Abstract

The cycloadditions of nitrone 2 to α,β-unsaturated lactones 3-6 have been studied under several reaction conditions. The adducts derived from pentenolide 5 and hexenolide 6 are the first examples of the pyrano[3,4-d]pyrrolo[1,2-b]isoxazole and oxepino[3,4-d]pyrrolo[1,2-b]isoxazole systems respectively. The stereochemistry of the products has been established using high field nmr techniques. In all cases the major cycloadduct derives from an exo orientation of the transition state. © 1993.
Original languageEnglish
Pages (from-to)4267-4274
JournalTetrahedron
Volume49
Issue number20
DOIs
Publication statusPublished - 1 Jan 1993

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