铱催化的羟基喹啉分子内不对称烯丙基烷基化反应：两个连续芳环芳香性的同时削弱。
Iridium-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Hydroxyquinolines: Simultaneous Weakening of the Aromaticity of Two Consecutive Aromatic Rings.
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 300072, China.
出版信息
J Am Chem Soc. 2018 Feb 28;140(8):3114-3119. doi: 10.1021/jacs.8b00136. Epub 2018 Feb 16.
Intramolecular asymmetric allylic alkylation reactions of 5- and 7-hydroxyquinoline derivatives were realized by a chiral Ir/NHC catalyst. A series of functionalized cyclic enones were afforded in excellent yields (up to 99%) and high enantioselectivity (up to 97% ee). Theoretical computations revealed that the aromaticity of the two consecutive rings of hydroxyquinoline substrates is significantly weakened. A highly efficient formal synthesis of (-)-gephyrotoxin was accomplished based on this method.
手性铱/NHC 催化剂实现了 5-和 7-羟基喹啉衍生物的分子内不对称烯丙基烷基化反应。一系列功能化环状烯酮以优异的收率（高达 99%）和高对映选择性（高达 97%ee）得到。理论计算表明，羟基喹啉底物的两个稠合环的芳香性显著减弱。在此方法的基础上，高效地完成了（-）-gephyrotoxin 的形式合成。
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