Ns strategies: a highly versatile synthetic method for amines
Ns strategies: a highly versatile synthetic method for amines
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DOI：
10.1039/b311203a
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发表时间：
2004-02-21
影响因子：
4.9
通讯作者：
Fukuyama, T
中科院分区：
文献类型：
--
作者：
Kan, T;Fukuyama, T
建立了一种以硝基苯磺酰胺作为保护基团和活化基团的高效、通用的胺合成方法。N-单取代N-酰胺的烷基化过程可以是常规的，也可以是在Mitsunobu条件下得到N，N-二取代的磺酰胺，并且N基很容易被亲核试剂通过Meisenheimer配合物去除，得到相应的仲胺。该方案的主要优点是烷基化和脱保护都在温和的条件下进行。因此，用这种方法，可以有效地完成线性和/或大环天然多胺的全合成。
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.