• 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

Rh(I)/Sc(OTf)共催化铵叶立德与(E)-1,4-烯二酮的迈克尔加成反应:功能化 1,4-二酮的合成。

Rh(I)/Sc(OTf)-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones.

机构信息

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.

Key Laboratory of Green Chemistry and Technology Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.

出版信息

Mol Divers. 2019 Nov;23(4):997-1010. doi: 10.1007/s11030-019-09941-8. Epub 2019 Apr 5.

DOI:10.1007/s11030-019-09941-8
PMID:30953296
Abstract

A Rh(I)/Sc(III) co-catalyzed synthesis of highly valuable functionalized 1,4-diketone derivatives in good yields and with an excellent diastereoselectivity. The established method provides a rapid approach to structurally diverse 1,4-diketone scaffold in a very mild and rapid fashion from simple starting materials. Moreover, the protocol could be easily scaled up to gram-scale synthesis. An attempt to develop an asymmetric version of the Rh(I)/guanidine system was also explored, resulting in a moderate enantioselectivity (71% ee).

摘要

铑(I)/钪(III)协同催化高附加值功能化 1,4-二酮衍生物的合成,产率高,非对映选择性好。该方法从简单的起始原料出发,以温和、快速的方式提供了一种构建结构多样的 1,4-二酮骨架的快速方法。此外,该方案可以很容易地放大到克级规模的合成。还尝试开发了不对称的铑(I)/胍体系,得到了中等的对映选择性(71%ee)。

相似文献

1
Rh(I)/Sc(OTf)-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones.Rh(I)/Sc(OTf)共催化铵叶立德与(E)-1,4-烯二酮的迈克尔加成反应:功能化 1,4-二酮的合成。
Mol Divers. 2019 Nov;23(4):997-1010. doi: 10.1007/s11030-019-09941-8. Epub 2019 Apr 5.
2
An ylide transformation of rhodium(I) carbene: enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates.铑(I)卡宾的叶立德转化:通过β-硝基丙烯酸酯捕获与铑(I)相关的铵叶立德实现对映选择性的三组分反应。
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13136-9. doi: 10.1002/anie.201407740. Epub 2014 Oct 5.
3
Sc(OTf)3-catalyzed indolylation of 1,2-allenic ketones: controlled highly selective synthesis of beta-indolyl-alpha,beta-unsaturetated (E)-enones and beta,beta-bisindolyl ketones.三氟甲磺酸钪催化的1,2-联烯酮的吲哚化反应:β-吲哚基-α,β-不饱和(E)-烯酮和β,β-双吲哚基酮的可控高选择性合成
Org Lett. 2005 Oct 27;7(22):5063-5. doi: 10.1021/ol052073z.
4
Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones.Sc(OTf)3 催化吲哚合成和 SnCl4 介导的 5-(芳基氨基)戊-3-炔-2-酮区域选择性氯化反应。
J Org Chem. 2011 Oct 21;76(20):8329-35. doi: 10.1021/jo201514q. Epub 2011 Sep 16.
5
Highly Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to Simple Aryl Ketones: Efficient Synthesis of Escitalopram.铑催化芳基硼酸酯对简单芳基酮的高对映选择性加成:艾司西酞普兰的高效合成
Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4527-31. doi: 10.1002/anie.201600979. Epub 2016 Mar 2.
6
Scandium cation-exchanged montmorillonite catalyzed direct C-glycosylation of a 1,3-diketone, dimedone, with unprotected sugars in aqueous solution.钪阳离子交换蒙脱石催化1,3 -二酮(达米酮)与未保护的糖类在水溶液中直接进行C-糖基化反应。
Carbohydr Res. 2007 May 21;342(7):913-8. doi: 10.1016/j.carres.2007.01.013. Epub 2007 Jan 31.
7
Chiral Sc-catalyzed asymmetric Michael reactions of thiols with enones in water.手性 Sc 催化的硫醇与烯酮在水中的不对称迈克尔反应。
Org Biomol Chem. 2011 May 21;9(10):3619-21. doi: 10.1039/c1ob05424d. Epub 2011 Apr 7.
8
Sc(OTf)3-catalyzed efficient synthesis of beta,beta-bis(indolyl) ketones by the double indolylation of acetic acid 2-methylene-3-oxobutyl ester.三氟甲磺酸钪催化2-亚甲基-3-氧代丁酸乙酯经双吲哚化反应高效合成β,β-双(吲哚基)酮
Org Biomol Chem. 2005 May 21;3(10):1933-6. doi: 10.1039/b503378k. Epub 2005 Apr 14.
9
Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex.高对映选择性合成 3-氨基-2-氧吲哚衍生物:手性钪配合物催化 3-取代 2-氧吲哚的不对称α-胺化反应。
Chemistry. 2010 Jun 11;16(22):6632-7. doi: 10.1002/chem.201000126.
10
Rhodium(I)-catalyzed synthesis of indoles: amino-Claisen rearrangement of N-propargylanilines.铑(I)催化吲哚的合成:N-炔丙基苯胺的氨基克莱森重排反应
J Org Chem. 2009 Feb 20;74(4):1517-24. doi: 10.1021/jo8022523.

引用本文的文献

1
A diastereoselective three-component reaction for the assembly of succinimide and isatin hybrid molecules with potent anticancer activities.一种用于构建具有强效抗癌活性的琥珀酰亚胺和异吲哚酮杂化分子的非对映选择性三组分反应。
Mol Divers. 2023 Apr;27(2):837-843. doi: 10.1007/s11030-022-10457-x. Epub 2022 Jun 6.
2
Multicomponent Reactions Involving Diazo Reagents: A 5-Year Update.多组分反应涉及重氮试剂:5 年更新。
Molecules. 2021 Oct 29;26(21):6563. doi: 10.3390/molecules26216563.

本文引用的文献

1
Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles.金属催化非有机金属亲核试剂的不对称1,4-共轭加成(ACA)的最新进展
Chem Rev. 2018 Aug 22;118(16):7586-7656. doi: 10.1021/acs.chemrev.7b00692. Epub 2018 Jul 26.
2
Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined β-Arylpyrrolidines.铑催化的分子间 C-H 功能化作为合成复杂立体定义的β-芳基吡咯烷的关键步骤。
Org Lett. 2018 Jul 6;20(13):3771-3775. doi: 10.1021/acs.orglett.8b01362. Epub 2018 Jun 21.
3
Control of Selectivity in Palladium(II)-Catalyzed Oxidative Transformations of Allenes.
钯(II)催化的丙二烯氧化转化反应中选择性的控制
Acc Chem Res. 2018 Jun 19;51(6):1520-1531. doi: 10.1021/acs.accounts.8b00138. Epub 2018 May 24.
4
Acetylenes in the Superbase-Promoted Assembly of Carbocycles and Heterocycles.超碱促进的碳环和杂环组装中的乙炔
Acc Chem Res. 2018 May 15;51(5):1117-1130. doi: 10.1021/acs.accounts.7b00618. Epub 2018 Apr 18.
5
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis.三甲基硅基保护炔烃作为钛催化[2+2+1]吡咯合成中选择性交叉偶联伙伴。
Angew Chem Int Ed Engl. 2018 May 22;57(21):6090-6094. doi: 10.1002/anie.201800595. Epub 2018 Apr 25.
6
Catalytic Asymmetric β-C-H Functionalizations of Ketones via Enamine Oxidation.酮的烯胺氧化催化不对称 β-C-H 官能化。
Org Lett. 2018 Mar 16;20(6):1672-1675. doi: 10.1021/acs.orglett.8b00508. Epub 2018 Mar 7.
7
A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules.多环分子的汇聚和立体选择性组装策略。
J Am Chem Soc. 2018 Feb 7;140(5):1956-1965. doi: 10.1021/jacs.7b13234. Epub 2018 Jan 24.
8
A DFT calculation-inspired Rh(i)-catalyzed reaction suppression of α-H shift in α-alkyldiazoacetates.一种受密度泛函理论(DFT)计算启发的铑(I)催化反应——抑制α-烷基重氮乙酸酯中的α-H迁移。
Chem Sci. 2017 Jun 1;8(6):4312-4317. doi: 10.1039/c7sc00257b. Epub 2017 Mar 22.
9
Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4-pyrazol-4-ones.5-酰基-5-苯基-1,5-二氢-4-吡唑-4-酮对多胺和氨基糖苷的高选择性酰化作用
Chem Sci. 2017 Oct 1;8(10):7152-7159. doi: 10.1039/c7sc03184j. Epub 2017 Aug 30.
10
Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N'-Dioxide-Metal Complexes.手性 N,N'-二氧代合金属配合物催化的不对称环加成和环化反应。
Acc Chem Res. 2017 Oct 17;50(10):2621-2631. doi: 10.1021/acs.accounts.7b00377. Epub 2017 Oct 2.