First example of a third generation nitrone cycloaddition

Pedro De March, Marta Figueredo, Josep Font, Sergio Milán, Angel Alvarez-Larena, Juan F. Piniella, Elies Molins

Research output: Contribution to journalArticleResearchpeer-review

24 Citations (Scopus)

Abstract

Compounds 5 and 6, derived from the cycloadditions of a nitrone to α,β-unsaturated lactones, were oxidized with m-chloroperbenzoic acid affording regiospecifically aldonitrones, 8 and 14, respectively. These second generation nitrones were reacted with several dipolarophiles yielding cycloadducts 9-13, 15, and 16. A repeated sequence of oxidation-cycloaddition applied to compound 12 allowed the isolation of die first example of a third generation cycloadduct, 17. During this work a series of new highly functionalized pyrrolidines have been prepared.
Original languageEnglish
Pages (from-to)2979-2988
JournalTetrahedron
Volume53
Issue number8
DOIs
Publication statusPublished - 24 Feb 1997

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