Jung Hyung Hoon, Floreancig Paul E
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Org Lett. 2006 Apr 27;8(9):1949-51. doi: 10.1021/ol060574u.
[reaction: see text] 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 alpha,beta-unsaturated ketones.
[反应：见正文] 带有侧链亲核试剂的高炔丙基醚在水性溶剂中使用金催化剂时，可生成杂环酮。这些反应效率高、对官能团和环境气氛具有耐受性且操作简单。非对映选择性可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，它们可在高度选择性条件下被解开，通过对α,β-不饱和酮进行亲核加成来促进杂环形成。
