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 language | English (US) |
|---|---|
| Pages (from-to) | 3419-3422 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 42 |
| Issue number | 20 |
| DOIs | |
| State | Published - May 14 2001 |
Keywords
- Cope elimination
- Hydroxylamines
- N-oxide
- Solid-phase synthesis
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Cite this
Sammelson, R. E., & Kurth, M. J. (2001). Oxidation-Cope elimination: A REM-resin cleavage protocol for the solid-phase synthesis of hydroxylamines. Tetrahedron Letters, 42(20), 3419-3422. https://doi.org/10.1016/S0040-4039(01)00477-4