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

✍ Scribed by Robert E Sammelson; Mark J Kurth

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 142 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00477-4

✦ Synopsis

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.