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Issue 4, 2004
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Ns strategies: a highly versatile synthetic method for amines

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Abstract

A highly efficient and versatile synthetic method for amines was established using nitrobenzenesulfonamides (Ns-amides) as both a protecting and activating group. The alkylation of N-monosubstituted Ns-amides either proceeded conventionally or under Mitsunobu conditions to provide the N,N-disubstituted sulfonamides, and the Ns group was removed easily with soft nucleophiles via Meisenheimer complexes to give the corresponding secondary amines. The major advantage of this protocol is that both alkylation and deprotection proceed under mild conditions. Thus, with this methodology, the total synthesis of linear and/or macrocyclic natural polyamines can be accomplished efficiently.

Graphical abstract: Ns strategies: a highly versatile synthetic method for amines

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Article information


Submitted
12 Sep 2003
Accepted
28 Oct 2003
First published
25 Nov 2003

Chem. Commun., 2004, 353-359
Article type
Feature Article

Ns strategies: a highly versatile synthetic method for amines

T. Kan and T. Fukuyama, Chem. Commun., 2004, 353
DOI: 10.1039/B311203A

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