An oxidatively-activated safety catch linker for solid phase synthesis

Stephen G. Davies, Duncan A. B. Mortimer, AndrewW. Mulvaney, Angela J. Russell, Hjalmar Skarphedinsson, Andrew D. Smith, Richard J. Vickers

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively activated safety catch linker for reaction monitoring and optimisation on solid support. The CAN promoted oxidative debenzylation of the tertiary N-benzylamine moiety, followed by concomitant cyclisation and release of alcohols and amines has been demonstrated both in solution phase model studies and on the solid phase. The linker system has been applied to the solid phase synthesis of a collection of phenol derivatives, and to the demonstration of the attachment and release of a chiral auxiliary from a solid support.

Original languageEnglish
Pages (from-to)1625-1634
Number of pages10
JournalOrganic & Biomolecular Chemistry
Volume6
Issue number9
DOIs
Publication statusPublished - 2008

Keywords

  • SUPPORTED CHIRAL AUXILIARY
  • ASYMMETRIC ALKYLATION REACTIONS
  • ORGANIC-SYNTHESIS
  • SECONDARY-AMINES
  • COMBINATORIAL CHEMISTRY
  • POLYKETIDE LIBRARIES
  • EVANS OXAZOLIDINONE
  • ADDITION-REACTIONS
  • PEPTIDE SYNTHESIS
  • ACID-DERIVATIVES

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