Selective Synthesis of β-Alkylpyrroles
Selective Synthesis of β-Alkylpyrroles
复制标题
β-烷基吡咯的选择性合成
DOI：
10.1002/chem.201002248
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发表时间：
2011
期刊：
影响因子：
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通讯作者：
Teruhisa Tsuchimoto
中科院分区：
文献类型：
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作者：
Naoki Yoshida;Masato Noguchi;Tomonari Tanaka;Takeshi Matsumoto;Naoya Aida;Masaki Ishihara;Atsushi Kobayashi;Shin-ichiro Shoda;Teruhisa Tsuchimoto
β-烷基吡咯是许多天然产物、生物活性化合物以及功能有机材料中的关键结构基元。由于这个原因，合成化学家继续对构建β-烷基吡咯的框架感兴趣。由于吡咯具有足够的芳香性和过量的π性质，合成β-烷基吡咯的直接方法应该是对吡咯环进行亲电芳香取代(SEAR)。然而，由于吡咯的主要亲核位置是α-位置，因此需要一些“技巧”来引导进入的烷基亲电分子朝向β-位置。这篇概念性文章重点介绍了以前致力于合成β-烷基吡咯的努力，主要是通过SEAR路线。
β‐Alkylpyrroles are key structural motifs found in many natural products and biologically active compounds as well as functional organic materials. For this reason, synthetic chemists continue to be interested in construction of the framework of β‐alkylpyrroles. Due to sufficient aromaticity and π‐excessive nature of pyrroles, a straightforward approach to β‐alkylpyrroles should be electrophilic aromatic substitution (SEAr) toward the pyrrole ring. However, since a primary nucleophilic site of pyrroles is an α‐position, some “trick” is required to direct incoming alkyl electrophiles toward a β‐position. This Concept article focuses on presenting previous efforts that have been devoted to the synthesis of β‐alkylpyrroles, mainly through the SEAr route.