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

doi:10.1016/S1872-2067(14)60204-7

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 68-77.DOI: 10.1016/S1872-2067(14)60204-7

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

刘堂林^a, 李清华^a, 何照林^a, 张佳伟^a, 王春江^a,b

a 武汉大学化学与分子科学学院, 湖北武汉430072 ;
b 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

收稿日期:2014-06-26 修回日期:2014-07-22 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 王春江
基金资助:
国家重点基础研究发展计划(973计划, 2011CB808600); 国家自然科学基金(21172176, 21372180); 湖北省高等学校科研基金资助项目(ZRZ0273); 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(5052011203011).

Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides

Tanglin Liu^a, Qinghua Li^a, Zhaolin He^a, Jiawei Zhang^a, Chunjiang Wang^a,b

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

Received:2014-06-26 Revised:2014-07-22 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Basic Research Program of China (973 Program, 2011CB808600), the National Natural Science Foundation of China (21172176, 21372180), Hubei Province Natural Science Foundation (ZRZ0273), Fundamental Research Funds for the Central Universities, and an Academic Award for Excellent PhD Candidates Funded by the Ministry of Education of China (5052011203011).

摘要/Abstract

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.

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

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).

Key words: Asymmetric catalysis, Quaternary stereogenic center, 1,3-Dipolar cycloaddition, Azomethine ylide, Cyclopropylidene acetate, 5-Aza-spiro[2,4]heptane

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.

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.

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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

Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides

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