化学
吡咯烷
炔烃
表面改性
反应性(心理学)
四氢异喹啉
炔基化
有机合成
乙炔
芳基
电化学
双环分子
有机化学
缩醛
组合化学
烷基
催化作用
替代医学
物理化学
病理
医学
电极
出处
期刊:Tetrahedron
[Elsevier]
日期:1984-01-01
卷期号:40 (5): 811-850
被引量:336
标识
DOI:10.1016/s0040-4020(01)91472-3
摘要
A synthetic route for the preparation of alkynylated saturated N‐heterocycles via a sequential combination of a Shono oxidation and a gold(I)‐catalyzed alkynylation reaction has been developed. The electrochemical Shono oxidation allowed an efficient access to a variety of N,O‐acetals via a direct C−H bond functionalization of cyclic amines. The reaction conditions were amenable with functionalized pyrrolidine, tetrahydroisoquinoline and pyrrolidine‐cyclopropyl fused bicyclic skeletons. The gold‐catalyzed process allowed the introduction of aryl acetylene partners bearing electron‐donating and moderate electron‐withdrawing. The efficiency of the gold process is remarkable and could be scaled up to 5 mmol of N,O‐acetal. Post‐functionalization reactions were performed based on the reactivity of the alkyne, showing the broad interest of our methodology. Promising preliminary results on an asymmetric version were obtained (e.r. up to 84.5:15.5).
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