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Development of a new linker for the solid-phase synthesis of N-hydroxylated and N-methylated secondary amines


Pauli, Denise; Bienz, Stefan (2014). Development of a new linker for the solid-phase synthesis of N-hydroxylated and N-methylated secondary amines. Tetrahedron, 70(6):1348-1356.

Abstract

Merrifield resin was modified by the introduction of an ortho-nitrophenylethanal group that served as a linker moiety to attach amines to the resin by reductive amination. Resin-bound tertiary amines were shown to be readily transferred into the respective liberated N-hydroxylated or N-methylated derivatives by either an oxidation/Cope elimination or a permethylation/Hofmann elimination protocol. With these two divergent liberation/derivatization options, the new resin offers new flexibility in the solid phase synthesis of N-modified secondary amines, for instance in spider toxin synthesis.

Abstract

Merrifield resin was modified by the introduction of an ortho-nitrophenylethanal group that served as a linker moiety to attach amines to the resin by reductive amination. Resin-bound tertiary amines were shown to be readily transferred into the respective liberated N-hydroxylated or N-methylated derivatives by either an oxidation/Cope elimination or a permethylation/Hofmann elimination protocol. With these two divergent liberation/derivatization options, the new resin offers new flexibility in the solid phase synthesis of N-modified secondary amines, for instance in spider toxin synthesis.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:12 Feb 2015 13:02
Last Modified:08 Dec 2017 10:54
Publisher:Elsevier
ISSN:0040-4020
Publisher DOI:https://doi.org/10.1016/j.tet.2013.12.014

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