Oxidation-Cope elimination: A REM-resin cleavage protocol for the solid-phase synthesis of hydroxylamines

Robert E. Sammelson, Mark J. Kurth

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

We have established that using an oxidation-Cope elimination cleavage protocol allows for the synthesis of N,N-disubstituted hydroxylamines from REM resin (polymer-bound benzyl acrylate). Michael addition of a secondary amine or addition of a primary amine followed by reductive alkylation provides polymer-bound tertiary amines. Oxidation of these resin-bound tertiary amines with MCPBA is followed by concomitant Cope elimination to regenerate the polymer-bound acrylate and provide the cleaved hydroxylamines.

Original languageEnglish (US)
Pages (from-to)3419-3422
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number20
DOIs
StatePublished - May 14 2001

    Fingerprint

Keywords

  • Cope elimination
  • Hydroxylamines
  • N-oxide
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this