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
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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| Published in | 催化学报 Vol. 36; no. 1; pp. 68 - 77 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | Chinese |
| Published |
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
2015
武汉大学化学与分子科学学院,湖北武汉,430072%武汉大学化学与分子科学学院，湖北武汉430072 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0253-9837 1872-2067 |
| DOI | 10.1016/S1872-2067(14)60204-7 |
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| Abstract | 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. |
|---|---|
| AbstractList | 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. 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. |
| Abstract_FL | 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 sys‐tem 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 pyrroli‐dine ring in good yield (up to 97%) and high diastereoselectivity (95:5–>98:2 d.r) and excellent enantioselectivity (87%–98%ee). |
| Author | 刘堂林 李清华 何照林 张佳伟 王春江 |
| AuthorAffiliation | 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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| Author_FL | Tanglin Liu Zhaolin He Chunjiang Wang Jiawei Zhang Qinghua Li |
| Author_FL_xml | – sequence: 1 fullname: Tanglin Liu – sequence: 2 fullname: Qinghua Li – sequence: 3 fullname: Zhaolin He – sequence: 4 fullname: Jiawei Zhang – sequence: 5 fullname: Chunjiang Wang |
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| DOI | 10.1016/S1872-2067(14)60204-7 |
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| Keywords | 1,3-Dipolar cycloaddition 亚甲胺叶立德 1,3-偶极环加成 5-氮杂-2,4庚烷 Cyclopropylidene acetate 不对称催化 Asymmetric catalysis 5-Aza-spiro[2,4]heptane 季碳中心 亚环丙基乙酸乙酯 Quaternary stereogenic center Azomethine ylide |
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| Notes | 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 sys-tem 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 pyrroli-dine ring in good yield（up to 97%） and high diastereoselectivity（95：5–98：2 d.r） and excellent enantioselectivity（87%–98% ee）. Asymmetric catalysis Quaternary stereogenic center 1; 3‐Dipolar cycloaddition Azomethine ylide Cyclopropylidene acetate 5‐Aza‐spiro[2; 4]heptane Tanglin Liu,Qinghua Li,Zhaolin He,Jiawei Zhang,Chunjiang Wanga College of Chemistry and MolecularSciences, Wuhan University, Wuhan 430072, Hubei, China b State Key Laboratory of O |
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| PublicationTitle | 催化学报 |
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| Publisher | 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 武汉大学化学与分子科学学院,湖北武汉,430072%武汉大学化学与分子科学学院，湖北武汉430072 |
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| Snippet | 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... 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... |
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| SubjectTerms | 1,3-偶极环加成 5-氮杂-[2,4]庚烷 不对称催化 亚环丙基乙酸乙酯 亚甲胺叶立德 季碳中心 |
| Title | 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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