Gold-catalyzed heterocycle synthesis using homopropargylic ethers as latent electrophiles.
Gold-catalyzed heterocycle synthesis using homopropargylic ethers as latent electrophiles.
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使用均炔醚作为潜在亲电子试剂进行金催化杂环合成。
DOI：
10.1021/ol060574u
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发表时间：
2006
期刊：
影响因子：
5.2
通讯作者：
Floreancig,PaulE
中科院分区：
文献类型：
--
作者：
Jung,HyungHoon;Floreancig,PaulE
当在水性溶剂中与Au催化剂接触时，具有亲核侧基的高炔丙基醚提供杂环酮。该反应是有效的，耐受官能度和环境气氛，并且操作简单。非对映选择性可以根据产物热力学进行预测。该过程证明了高炔丙基醚作为潜在亲电试剂的可行性，其可以在高度选择性条件下被解开，以通过亲核加成至α，β-不饱和酮来促进杂环形成。
Homopropargylic ethers with pendent nucleophiles, when subjected to Au catalysts in aqueous solvent, provide heterocyclic ketones. The reactions are efficient, tolerant of functionality and ambient atmosphere, and operationally simple. Diastereoselectivity can be predicted on the basis of product thermodynamics. This process demonstrates the viability of homopropargylic ethers to serve as latent electrophiles that can be unraveled under highly selective conditions to promote heterocycle formation through nucleophilic additions to α,β-unsaturated ketones.