手性布朗斯特酸在低催化剂负载量下催化4,7-二氢吲哚与硝基烯烃的不对称傅克反应。
Asymmetric Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins by chiral Brønsted acids under low catalyst loading.
作者信息
Sheng Yi-Fei, Li Gong-Qiang, Kang Qiang, Zhang An-Jiang, You Shu-Li
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 54 Fenglin Lu, Shanghai, China.
出版信息
Chemistry. 2009;15(14):3351-4. doi: 10.1002/chem.200900033.
Slowly does it! By adding the substrate by a syringe pump, a highly efficient Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins was realized with 0.5 mol % of a chiral phosphoric acid. The Friedel-Crafts alkylation, together with a subsequent oxidation of the product, led to 2-substituted indoles in excellent enantiomeric excesses, which can be easily transformed to enantioenriched tetrahydro-gamma-carbolines.
慢慢来！通过用注射泵添加底物，在手性磷酸0.5 mol%的作用下，实现了4,7-二氢吲哚与硝基烯烃的高效傅克反应。傅克烷基化反应以及产物随后的氧化反应，以优异的对映体过量得到了2-取代吲哚，其可轻松转化为对映体富集的四氢-γ-咔啉。
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