吲哚
化学
催化作用
过氧化物
键裂
铜
组合化学
氧气
过氧化氢
反应性(心理学)
光化学
有机化学
医学
替代医学
病理
作者
Ying Peng,Wei Wang,Jun Shi,Wei Wu,Jiahui Song,Weidong Pan,Ge‐Fei Hao,Hai Ren
标识
DOI:10.1002/ange.202313687
摘要
Abstract Herein, we report an unprecedented skeletal rearrangement reaction of tetrahydro‐ β ‐carbolines enabled by copper‐catalyzed single‐electron oxidative oxygenation, in which H 2 O and O 2 act as oxygen sources to generate a unique 2‐hydroxyl‐3‐peroxide indoline intermediate. The synthetic reactivity of 2‐hydroxyl‐3‐peroxide indoline species was demonstrated by a unique multi‐step bond cleavage and formation cascade. Using a readily available copper catalyst under open‐air conditions, highly important yet synthetically difficult spiro[pyrrolidone‐(3,1‐benzoxazine)] products were obtained in a single operation. The synthetic utility of this methodology is demonstrated by the efficient synthesis of the natural products donaxanine and chimonamidine, as well as the 3‐hydroxyl‐pyrroloindoline scaffold, in just one or two steps.
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