Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

Demetrios Agathocleous, Graham Cox, Michael I. Page

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P-exo-succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by 1H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.

Original languageEnglish
Pages (from-to)1631-1634
Number of pages4
JournalTetrahedron Letters
Volume27
Issue number14
DOIs
Publication statusPublished - 1986

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