• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

钯催化乙烯基环丙烷与亚胺的高度对映选择性环加成反应

Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines.

作者信息

Huang Xiao-Bing, Li Xian-Jing, Li Tian-Tian, Chen Bo, Chu Wen-Dao, He Long, Liu Quan-Zhong

机构信息

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering , China West Normal University , No. 1, Shida Road , Nanchong 637002 , P.R. China.

College of Pharmaceutical Sciences , Guizhou University of Chinese Medicine , Guiyang 550025 , P.R. China.

出版信息

Org Lett. 2019 Mar 15;21(6):1713-1716. doi: 10.1021/acs.orglett.9b00274. Epub 2019 Mar 4.

DOI:10.1021/acs.orglett.9b00274
PMID:30829043
Abstract

Palladium-catalyzed asymmetric formal [3 + 2] cycloaddition of vinyl cyclopropanes and aldimines or isatin-derived ketimines proceeded smoothly in the presence of chiral phosphoramidite ligands. The corresponding highly functionalized and optically enriched pyrrolidine or spiro[pyrrolidin-3,2'-oxindole] derivatives are obtained in up to 94% yield and with up to 96% ee and 7:1 dr.

摘要

在手性亚磷酰胺配体存在下，钯催化乙烯基环丙烷与醛亚胺或异吲哚酮衍生的酮亚胺进行不对称形式的[3 + 2]环加成反应顺利进行。相应的高度官能化且光学富集的吡咯烷或螺[吡咯烷-3,2'-氧化吲哚]衍生物的产率高达94%，对映体过量率高达96%，非对映体比例为7:1。

相似文献

1
Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines.钯催化乙烯基环丙烷与亚胺的高度对映选择性环加成反应
Org Lett. 2019 Mar 15;21(6):1713-1716. doi: 10.1021/acs.orglett.9b00274. Epub 2019 Mar 4.
2
Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines.通过席夫碱催化的螺[氧化吲哚-吡咯烷-噁唑啉]衍生物与 N-(2,2,2-三氟乙基)邻苯二甲酰亚胺酮的双迈克尔/曼尼希[3+2]环加成反应构建非对映选择性双螺[氧化吲哚-吡咯烷-噁唑啉]
J Org Chem. 2018 Aug 17;83(16):9278-9290. doi: 10.1021/acs.joc.8b01245. Epub 2018 Jul 9.
3
Palladium-catalyzed asymmetric cycloadditions of vinylcyclopropanes and in situ formed unsaturated imines: construction of structurally and optically enriched spiroindolenines.钯催化的乙烯基环丙烷与原位生成的不饱和亚胺的不对称环加成反应：结构和光学均富集的螺吲哚啉的构建。
Org Lett. 2015 Jan 2;17(1):150-3. doi: 10.1021/ol503383x. Epub 2014 Dec 19.
4
Enantioselective construction of pyrrolidines by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethane with imines.钯催化三烯甲烷与亚胺的不对称 [3 + 2] 环加成反应构建手性吡咯烷。
J Am Chem Soc. 2012 Mar 14;134(10):4941-54. doi: 10.1021/ja210981a. Epub 2012 Mar 2.
5
Chiral Brønsted Base Activation of Donor-Acceptor Cyclopropanes toward Diastereo- and Enantioselective [3 + 2] Cycloaddition with Isatin-Derived Ketimines.手性布朗斯特碱活化给体-受体环丙烷与异吲哚酮衍生的酮亚胺进行非对映和对映选择性[3 + 2]环加成反应
J Org Chem. 2024 Jun 21;89(12):8691-8705. doi: 10.1021/acs.joc.4c00614. Epub 2024 Jun 10.
6
Enantioselective construction of highly substituted pyrrolidines by palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with ketimines.钯催化三甲基烯丙基甲烷与亚胺的不对称 [3+2] 环加成反应构建高取代吡咯烷。
J Am Chem Soc. 2010 Jun 23;132(24):8238-40. doi: 10.1021/ja102102d.
7
Organocatalyzed asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans and N-2,2,2-trifluoroethylisatin ketimines.有机催化不对称去芳构化 1,3-偶极环加成反应：2-硝基苯并呋喃和 N-2,2,2-三氟乙基亚氨基靛红酮。
Chirality. 2022 Jul;34(7):1019-1034. doi: 10.1002/chir.23455. Epub 2022 May 6.
8
Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3'-oxindole] framework.甲亚胺叶立德与异吲哚酮衍生的亚胺的催化不对称化学选择性1,3-偶极环加成反应：螺[咪唑烷-2,3'-异吲哚酮]骨架的非对映和对映选择性构建
Chem Commun (Camb). 2016 Jan 31;52(9):1804-7. doi: 10.1039/c5cc07924a.
9
Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines.通过钯催化的乙烯基苯并恶嗪酮与磺酰胺衍生的环亚胺的[4 + 2]环加成反应，对映选择性构建四氢喹唑啉基序。
Org Lett. 2018 May 18;20(10):2880-2883. doi: 10.1021/acs.orglett.8b00905. Epub 2018 May 7.
10
Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.手性 N-杂环卡宾催化的高对映选择性烯醛与色酮衍生的亚胺的加成：螺环γ-内酰胺的合成。
Org Lett. 2012 Nov 2;14(21):5412-5. doi: 10.1021/ol302475g. Epub 2012 Oct 12.

引用本文的文献

1
Asymmetric Three-Component Radical Cascade Reactions Enabled by Synergistic Photoredox/Brønsted Acid Catalysis: Access to α-Amino Acid Derivatives.协同光氧化还原/布朗斯特酸催化实现的不对称三组分自由基串联反应：合成α-氨基酸衍生物
ACS Cent Sci. 2024 Aug 16;11(1):36-45. doi: 10.1021/acscentsci.4c00970. eCollection 2025 Jan 22.
2
Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes.钯催化的源自氨基磺酸酯亚胺的1-氮杂二烯与螺环环戊烷的对映选择性和区域选择性（3 + 2）环加成反应。
Chem Sci. 2023 Apr 18;14(18):4893-4900. doi: 10.1039/d3sc01510f. eCollection 2023 May 10.
3
Palladium-catalyzed enantioselective rearrangement of dienyl cyclopropanes.
钯催化的二烯基环丙烷对映选择性重排反应。
Chem Sci. 2023 Mar 2;14(12):3346-3351. doi: 10.1039/d2sc06548g. eCollection 2023 Mar 22.
4
Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds oxa-Michael/1,6-conjugated addition of -quinone methides with benzofuranone-type olefins.含螺苯并呋喃酮骨架的色满的非对映选择性合成：醌甲基化物与苯并呋喃酮型烯烃的氧杂迈克尔/1,6-共轭加成反应。
RSC Adv. 2022 Jun 6;12(26):16684-16687. doi: 10.1039/d2ra03031d. eCollection 2022 Jun 1.
5
A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and -quinone methides: a facile synthesis of spirocyclic oxindole scaffolds.3-氯氧化吲哚与醌甲基化物的正式分子间[4 + 1]环加成反应：螺环氧化吲哚骨架的简便合成
RSC Adv. 2021 May 24;11(30):18576-18579. doi: 10.1039/d1ra01086g. eCollection 2021 May 19.
6
Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes.通过给体-受体环丙烷的发散级联反应合成咔唑和二氢咔唑。
Org Lett. 2021 Oct 1;23(19):7592-7596. doi: 10.1021/acs.orglett.1c02795. Epub 2021 Sep 20.
7
Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols.供体-受体环丙烷与2-萘酚的无过渡金属[3+2]脱水环加成反应
Front Chem. 2021 Jul 16;9:711257. doi: 10.3389/fchem.2021.711257. eCollection 2021.
8
Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes.钯催化利用乙烯基取代给体-受体环丙烷构建苯并[g]氧杂环庚烷的级联反应。
Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14410-14414. doi: 10.1002/anie.202102862. Epub 2021 May 26.
9
Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.过渡金属催化的乙烯基环丙烷在环加成反应中选择性碳-碳键断裂。
Chem Rev. 2021 Jan 13;121(1):110-139. doi: 10.1021/acs.chemrev.0c00160. Epub 2020 Aug 5.