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 › peer-review

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

Keywords

Cope elimination
Hydroxylamines
N-oxide
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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

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.",

keywords = "Cope elimination, Hydroxylamines, N-oxide, Solid-phase synthesis",

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TY - JOUR

T1 - Oxidation-Cope elimination

T2 - A REM-resin cleavage protocol for the solid-phase synthesis of hydroxylamines

AU - Sammelson, Robert E.

AU - Kurth, Mark J.

PY - 2001/5/14

Y1 - 2001/5/14

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.

KW - Cope elimination

KW - Hydroxylamines

KW - N-oxide

KW - Solid-phase synthesis

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U2 - 10.1016/S0040-4039(01)00477-4

DO - 10.1016/S0040-4039(01)00477-4

M3 - Article

AN - SCOPUS:0035858642

VL - 42

SP - 3419

EP - 3422

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 20

ER -