Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation
Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation
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DOI：
10.1021/acs.orglett.5b01312
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发表时间：
2015-07-03
期刊：
影响因子：
5.2
通讯作者：
Donohoe, Timothy J.
中科院分区：
文献类型：
--
作者：
Hardegger, Leo A.;Habegger, Jacqueline;Donohoe, Timothy J.
A，提出了基于钯催化的酮烯醇α-烯基化合成高度取代的吡啶的新方法；芳香族化合物的形成：是这种催化C-C键形成反应的新方向。在关键步骤中，受保护的β-卤代烯醛与酮参与α-烯基稀释，得到1,5-二羰基替代物，然后将其环化/双消去生成相应的吡啶：产物，所有这些都在一锅中进行。β-卤代烯醛起始材料可以通过相应的亚甲基酮获得 Vilsmeier 卤代甲酰化。使用这种简洁的路线，通过三步从市售化合物合成了多种高度取代的吡啶。
A, novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate alpha-alkenylation of ketones is presented; the formation of aromatic compounds: is: a new direction for this catalytic C-C bond forming reaction. In the, key step, a protected beta-haloalkenylaldehyde participates in alpha-alkenylution with a ketone to afford a 1,5-dicarbonyl surrogate,, which then undergoes cyclitation/double elimination to the corresponding pyridine:product, all in one pot., The beta-haloalkenylaldehyde starting materials can be obtained from the corresponding methylene ketone via Vilsmeier haloformylation. Using this concise route, a variety, of highly substituted pyridines were synthesized in three steps from commercially available compounds.