Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues

Jonathan Clayden*, Sean Parris, Nuria Cabedo, Andrew H. Payne

*Corresponding author for this work

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

27 Citations (Scopus)

Abstract

(Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.

Original languageEnglish
Pages (from-to)5060-5062
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number27
Early online date2 Jun 2008
DOIs
Publication statusPublished - 23 Jun 2008

Keywords

  • Carbohydrates
  • Dearomatization
  • Diastereoselectivity
  • Oxazolines
  • Pseudosugars

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