化学
对映选择合成
弗里德尔-克拉夫茨反应
磷酸
部分
催化作用
基质(水族馆)
吲哚试验
有机催化
有机化学
氢键
组合化学
立体化学
分子
海洋学
地质学
作者
Yuyang Ding,Dengfeng Xu,Shan‐Shui Meng,Yang Li,Junling Zhao
标识
DOI:10.1002/adsc.201701354
摘要
Abstract Through a hydrogen bonding guided substrate modification strategy, we have developed a chiral phosphoric acid catalyzed highly enantioselective Friedel‐Crafts reaction of N‐protected 4‐aminoindoles with β,γ‐unsaturated α‐ketimino esters. The mechanism and origins of the enantioselectivity of this process are indentified using DFT calculations. Both the experimental and calculation results indicated that the NH moiety at the indole C4 position is essential for the stereocontrol of this reaction. To further examine the potential usefulness of this method, gram scale synthesis and derivatizations of one of the products were also carried out. magnified image
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