Issue 4, 2004

Ns strategies: a highly versatile synthetic method for amines

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

Article information

Article type
Feature Article
Submitted
12 sept. 2003
Accepted
28 oct. 2003
First published
25 nov. 2003

Chem. Commun., 2004, 353-359

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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