Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.
Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.
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DOI：
10.1002/ejoc.201403615
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发表时间：
2015-03
影响因子：
2.8
通讯作者：
Fleming FF
中科院分区：
文献类型：
--
作者：
Lujan-Montelongo JA;Estevez AO;Fleming FF
亚磺酸烷基酯在曼尼希型反应中起形式亲核试剂的作用，得到磺酰基甲酰胺，其容易脱水成相应的磺酰基甲基异腈。有效的，两步合成提供了一个通用的路线磺酰基甲基异腈从容易获得的甲基亚磺酸酯或硫醇。机理分析表明，亚磺酸烷基酯的不寻常的亲核性来自于亚磺酸的原位释放。
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.