| 基于α-溴代酮的催化不对称合成3,3-螺环丙基吲哚酮和乙烯基环丙烷 |
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| 引用本文： | 罗京华,耿玮笙,曹仕轩,贺峥杰.基于α-溴代酮的催化不对称合成3,3-螺环丙基吲哚酮和乙烯基环丙烷[J].有机化学,2020(1):40-52. |
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| 作者姓名： | 罗京华 耿玮笙 曹仕轩 贺峥杰 |
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| 作者单位： | 南开大学化学学院;天津化学化工协同创新中心 |
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| 基金项目： | 国家自然科学基金(Nos.21472096,J1103306)资助项目。 |
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| 摘 要： | 在甲基化奎尼丁(20mol%)的催化下,分别实现了α-溴代酮与3-(取代亚甲基)吲哚酮和缺电子1,3-二烯的高度非对映选择性和对映选择性的环丙烷化反应,以46%~99%收率、高达98%ee和20∶1 dr生成相应的3,3-螺环丙基吲哚酮和乙烯基环丙烷.通过催化的氮叶立德策略,成功发展了一种用于上述手性化合物的简便合成方法.
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| 关 键 词： | 手性胺 [2+1]环化反应 α-溴代酮 不对称合成 |
Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones |
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| Luo Jinghua,Geng Weisheng,Cao Shixuan,He Zhengjie.Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones[J].Chinese Journal of Organic Chemistry,2020(1):40-52. |
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| Authors: | Luo Jinghua Geng Weisheng Cao Shixuan He Zhengjie |
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| Institution: | (State Key Laboratory of Elemento-organic Chemistry,College of Chemistry,Nankai University,Tianjin 300071;Collaborative Innovation Center of Chemical Science and Engineering(Tianjin),Tianjin 300071) |
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| Abstract: | Under the catalysis of chiral amine methylated quinidine, highly diastereo-and enantioselective cyclopropanation reactions of α-bromoketones with 3-(substituted methylene) oxindoles and electron-deficient 1,3-dienes have been realized respectively, providing corresponding functionalized 3,3-spirocyclopropyl oxindoles and vinylcyclopropanes in 46%~99% yields with up to 98% ee and up to 20∶1 dr. Thus, a facile and complementary synthetic method for chiral title compounds is successfully develped by the catalytic ammonium ylide strategy. |
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| Keywords: | chiral amine [2+1]annulation reaction α-bromoketone asymmetric synthesis |
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