Chiral Auxiliaries for Stereoselective Electrophilic Aromatic Substitutions
Chiral Auxiliaries for Stereoselective Electrophilic Aromatic Substitutions
复制标题
用于立体选择性亲电芳香取代的手性助剂
DOI：
10.1055/s-0040-1707296
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发表时间：
2021
期刊：
影响因子：
2
通讯作者：
Schneebeli, Severin T.
中科院分区：
文献类型：
--
作者：
Sharafi, Mona;Campbell, Joseph P.;Murphy, Kyle E.;Osadchey Brown, Reilly;Schneebeli, Severin T.
亲电芳香族取代反应对于生物活性化合物和其他先进材料的合成具有极其重要的意义。它们是无需过渡金属催化剂即可激活特定芳香族 C-H 键的重要手段。令人惊讶的是，亲电芳香取代的立体选择性变体很少，这限制了这些经典反应在立体选择性合成中的应用。虽然许多亲电芳族取代会产生非手性产物（由于芳环的平面性质），但也有产生手性产物的重要例子，包括芳香族环烷和具有多个芳环的前手性底物的去对称反应。这篇 Synpacts 文章现在阐述了当精确放置在离域碳阳离子上方和下方时，手性臂如何充当手性助剂，将经典的亲电芳香取代反应转化为强大的非对映和对映选择性转化。
Electrophilic aromatic substitution reactions are of profound importance for the synthesis of biologically active compounds and other advanced materials. They represent an important means to activate specific aromatic C–H bonds without requiring transition-metal catalysts. Surprisingly, few stereoselective variants are known for electrophilic aromatic substitutions, which limits the utility of these classical reactions for stereoselective synthesis. While many electrophilic aromatic substitutions lead to achiral products (due to the planar nature of aromatic rings), there are important examples where chiral products are produced, including desymmetrization reactions of aromatic cyclophanes and of prochiral substrates with multiple aromatic rings. ThisSynpactsarticle now illustrates how chiral arms, when placed precisely above and underneath delocalized carbocations, can act as chiral auxiliaries to convert classical electrophilic aromatic substitution reactions into powerful diastereo- and enantioselective transformations.
影响因子：
4.6
作者：
Botvay, A;Máthé, A;Pöppl, L
通讯作者：
Pöppl, L