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Solid-phase synthesis of cyclic polyamines


Bisegger, P; Manov, N; Bienz, S (2008). Solid-phase synthesis of cyclic polyamines. Tetrahedron, 64(32):7531-7536.

Abstract

A method for the synthesis of cyclic polyamines based on solid-phase chemistry is shown. Linear polyamines are stepwise synthesized on solid support from the center by repetitive alkylations at benzylic N-atoms. Cyclizations at the resins were effected conventionally by direct intramolecular SN2 reactions between sulfonyl-protected terminal amino groups and primary alkyl bromides or by intramolecular Mitsunobu reactions between sulphonamides and primary alcohols. Particularly the latter transformation proved to be powerful for the construction of medium- as well as large-sized rings.

Abstract

A method for the synthesis of cyclic polyamines based on solid-phase chemistry is shown. Linear polyamines are stepwise synthesized on solid support from the center by repetitive alkylations at benzylic N-atoms. Cyclizations at the resins were effected conventionally by direct intramolecular SN2 reactions between sulfonyl-protected terminal amino groups and primary alkyl bromides or by intramolecular Mitsunobu reactions between sulphonamides and primary alcohols. Particularly the latter transformation proved to be powerful for the construction of medium- as well as large-sized rings.

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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:August 2008
Deposited On:15 Feb 2009 10:23
Last Modified:18 Feb 2018 10:46
Publisher:Elsevier
ISSN:0040-4020
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/j.tet.2008.05.119

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