| 亚甲胺叶立德参与的不对称1,3-偶极环加成构建含连续季碳中心的螺四氢吡咯衍生物 |
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| 引用本文： | 刘堂林,李清华,何照林,张佳伟,王春江. 亚甲胺叶立德参与的不对称1,3-偶极环加成构建含连续季碳中心的螺四氢吡咯衍生物[J]. 催化学报, 2015, 36(1): 68-77. DOI: 10.1016/S1872-2067(14)60204-7 |
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| 作者姓名： | 刘堂林 李清华 何照林 张佳伟 王春江 |
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| 作者单位： | 1. 武汉大学化学与分子科学学院,湖北武汉,430072;2. 武汉大学化学与分子科学学院，湖北武汉430072; 中国科学院上海有机化学研究所有机金属化学国家重点实验室，上海230032 |
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| 基金项目： | the National Basic Research Program of China，the National Natural Science Foundation of China，Hubei Province Natural Science Foundation，Fundamental Research Funds for the Central Universities;and an Academic Award for Excellent PhD Candidates Funded by the Ministry of Education of China (5052011203011).基金来源:国家重点基础研究发展计划，国家自然科学基金，湖北省高等学校科研基金资助项目，中央高校基本科研业务费专项资金，教育部博士学术新人奖 |
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| 摘 要： | Cu(I)催化的亚甲胺叶立德和亚环丙基乙酸乙酯参与的不对称endo-1,3-偶极环加成反应,高效构建了多官能化、含有多个连续季碳中心的5-氮杂-[2,4]庚烷化合物.此反应具有广泛的底物适用性,α-取代的和α-非取代的亚甲胺叶立德和亚环丙基乙酸乙酯都能很好的参与反应,并以很高的产率、优秀的非对映选择性(95:5–98:2 d.r)和对映选择性(87%–98%ee)生成相应的在2,3,4位上含有连续季碳中心的螺四氢吡咯化合物.
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| 关 键 词： | 不对称催化 季碳中心 1,3-偶极环加成 亚甲胺叶立德 亚环丙基乙酸乙酯 5-氮杂-2,4庚烷 |
| 收稿时间： | 2014-06-26 |
Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides |
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| Tanglin Liu , Qinghua Li , Zhaolin He , Jiawei Zhang , Chunjiang Wang. Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides[J]. Chinese Journal of Catalysis, 2015, 36(1): 68-77. DOI: 10.1016/S1872-2067(14)60204-7 |
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| Authors: | Tanglin Liu Qinghua Li Zhaolin He Jiawei Zhang Chunjiang Wang |
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| Affiliation: | a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei, China;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 230032, China |
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| Abstract: | Bioactive 5-aza-spiro[2,4]heptanes with high functionality and up to three contiguous all-carbon quaternary stereogenic centers were synthesized by Cu(I)-catalyzed asymmetric endo-selective 1,3-dipolar cycloaddition of azomethine ylides with cyclopropylidene acetates. This synthesis system performs well for a broad scope of substrates. α-unsubstituted/α-substituted azomethine ylides and cyclopropylidene acetates are compatible 1,3-dipoles and dipolarophiles, which afford the spiro heterocycles with contiguous quaternary centers at 2-, 3- and 4-positions of the pyrrolidine ring in good yield (up to 97%) and high diastereoselectivity (95:5->98:2 d.r) and excellent enantioselectivity (87%-98% ee). |
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| Keywords: | Asymmetric catalysis Quaternary stereogenic center 1,3-Dipolar cycloaddition Azomethine ylide Cyclopropylidene acetate 5-Aza-spiro[2,4]heptane |
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