Dearomatizing disrotatory electrocyclic ring closure of lithiated N-benzoyloxazolidines

Jonathan Clayden*, Savroop Purewal, Madeleine Helliwell, Simon J. Mantell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

18 Citations (Scopus)

Abstract

Loss of aromaticity ensues when N-benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis-tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.

Original languageEnglish
Pages (from-to)1049-1051
Number of pages3
JournalAngewandte Chemie - International Edition
Volume41
Issue number6
DOIs
Publication statusPublished - 15 Mar 2002

Keywords

  • Amides
  • Cyclization
  • Lithiation
  • Pericyclic reaction
  • Stereoselectivity

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