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) |
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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