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

Robert E. Sammelson; Mark J. Kurth

doi:10.1016/S0040-4039(01)00477-4

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

Robert E. Sammelson, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	3419-3422
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(01)00477-4
State	Published - May 14 2001

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Keywords

Cope elimination
Hydroxylamines
N-oxide
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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

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AU - Kurth, Mark J.

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N2 - 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.

AB - 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.

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Access to Document

10.1016/S0040-4039(01)00477-4