• 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

高效金(I)/银(I)协同催化串联分子间 N-迈克尔加成/α-酮与未活化烯烃的分子内氢烷基化反应。

Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones.

机构信息

Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 , P. R. China.

出版信息

Beilstein J Org Chem. 2011;7:1100-7. doi: 10.3762/bjoc.7.126. Epub 2011 Aug 11.

DOI:10.3762/bjoc.7.126
PMID:21915213
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3170194/
Abstract

The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction conditions and the substrate scope of this reaction are examined, and a possible mechanism involving AgClO(4) catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed.

摘要

金(I)/银(I)协同催化的级联分子间 N-迈克尔加成/分子内氢烷基化反应为合成吡咯烷衍生物提供了一种简单高效的方法,产物收率中等至优秀,非对映选择性中等至良好。考察了该反应的反应条件和底物范围,并提出了一种可能的反应机理,涉及 AgClO4 催化的分子间 N-迈克尔加成和随后的金(I)催化的氢烷基化。

相似文献

1
Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones.高效金(I)/银(I)协同催化串联分子间 N-迈克尔加成/α-酮与未活化烯烃的分子内氢烷基化反应。
Beilstein J Org Chem. 2011;7:1100-7. doi: 10.3762/bjoc.7.126. Epub 2011 Aug 11.
2
Efficient gold(I)-catalyzed direct intramolecular hydroalkylation of unactivated alkenes with α-ketones.高效的金(I)催化未活化烯烃与α-酮的直接分子内氢烷基化反应。
Angew Chem Int Ed Engl. 2011 May 16;50(21):4937-41. doi: 10.1002/anie.201100044. Epub 2011 Apr 28.
3
Cationic Iridium Complex-Catalyzed Intermolecular Hydroalkylation of Unactivated Alkenes with 1,3-Diketones.阳离子铱配合物催化的 1,3-二酮与非活化烯烃的分子间氢烷基化反应。
Org Lett. 2019 Feb 1;21(3):741-744. doi: 10.1021/acs.orglett.8b03975. Epub 2019 Jan 14.
4
Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives.3-硝基-2H-色烯与开链烯酮的对映选择性串联双迈克尔加成反应:官能团化三环色满衍生物的高效合成
Org Biomol Chem. 2015 Oct 7;13(37):9600-9. doi: 10.1039/c5ob01211b.
5
Gold(I)- and Yb(OTf)(3)-cocatalyzed rearrangements of epoxy alkynes: transfer of a carbonyl group in a five-membered carbocycle.金(I)-和 Yb(OTf)(3)-共催化的环氧炔烃重排:在五元碳环中转移羰基。
Chemistry. 2010 Feb 22;16(8):2496-502. doi: 10.1002/chem.200902321.
6
Gold-Catalyzed Addition of β-Ketoesters to Alkenes: Influence of Electronic and Steric Effects in the Reaction Outcome.金催化的β-酮酯与烯烃的加成反应:反应结果中电子和空间效应的影响。
Molecules. 2018 Mar 10;23(3):629. doi: 10.3390/molecules23030629.
7
Nickel-Catalyzed α-selective Hydroalkylation of Vinylarenes.镍催化的乙烯基芳烃的α-选择性氢烷基化反应
Angew Chem Int Ed Engl. 2024 Nov 18;63(47):e202413074. doi: 10.1002/anie.202413074. Epub 2024 Oct 14.
8
Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines.用于合成手性三取代吡咯烷的方酰胺催化的不对称串联氮杂-Michael/Michael加成反应
Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a.
9
Iridium-Catalyzed Hydroalkylation of Aliphatic Alkenes with β-Ketoesters: Formal Hydroalkylation with Methyl Ketones.铱催化脂肪族烯烃与β-酮酯的氢烷基化反应:与甲基酮的形式氢烷基化反应
Org Lett. 2020 Aug 7;22(15):6187-6191. doi: 10.1021/acs.orglett.0c02291. Epub 2020 Jul 22.
10
Palladium-Catalyzed Asymmetric Cascade Intramolecular Cyclization/Intermolecular Michael Addition Reaction of Allenyl Benzoxazinones with 1-Azadienes.钯催化的烯丙基苯并恶嗪酮与 1-氮杂二烯的不对称级联分子内环化/分子间迈克尔加成反应。
Org Lett. 2022 Dec 30;24(51):9442-9446. doi: 10.1021/acs.orglett.2c03842. Epub 2022 Dec 20.

引用本文的文献

1
Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.通过未活化烯烃的氢烷基化反应合成季碳中心的方法:二十年的进展
Beilstein J Org Chem. 2021 Jul 7;17:1565-1590. doi: 10.3762/bjoc.17.112. eCollection 2021.
2
Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.通过单-N-丙烯酰基炔丙基胍的级联氢胺化/迈克尔加成反应合成双环胍。
Org Lett. 2014 Dec 5;16(23):6048-51. doi: 10.1021/ol502691w. Epub 2014 Nov 13.
3
New developments in gold-catalyzed manipulation of inactivated alkenes.

本文引用的文献

1
Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes.通过未活化烯烃的分子内氨基金化反应制备烷基金配合物。
Chem Sci. 2010 Aug 1;1(2). doi: 10.1039/C0SC00255K.
2
Efficient gold(I)-catalyzed direct intramolecular hydroalkylation of unactivated alkenes with α-ketones.高效的金(I)催化未活化烯烃与α-酮的直接分子内氢烷基化反应。
Angew Chem Int Ed Engl. 2011 May 16;50(21):4937-41. doi: 10.1002/anie.201100044. Epub 2011 Apr 28.
3
Gold-catalyzed carbon-heteroatom bond-forming reactions.金催化的碳-杂原子成键反应。
金催化的失活烯烃的转化研究新进展。
Beilstein J Org Chem. 2013 Nov 21;9:2586-614. doi: 10.3762/bjoc.9.294.
Chem Rev. 2011 Mar 9;111(3):1657-712. doi: 10.1021/cr100414u.
4
Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles.金催化功能化丙二烯的亲核环化反应:构建碳环和杂环的有效方法
Chem Rev. 2011 Mar 9;111(3):1994-2009. doi: 10.1021/cr1004088. Epub 2011 Feb 11.
5
Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds.金催化芳烃和杂芳烃与 C-C 多重键的修饰。
Chem Soc Rev. 2011 Mar;40(3):1358-67. doi: 10.1039/c0cs00041h. Epub 2010 Nov 22.
6
Homogeneous gold catalysis beyond assumptions and proposals--characterized intermediates.均相金催化超越假设与设想——特性中间体。
Angew Chem Int Ed Engl. 2010 Jul 19;49(31):5232-41. doi: 10.1002/anie.200907078.
7
Gold-catalyzed synthesis of nitrogen-containing heterocycles from epsilon-N-protected propargylic esters.金催化的ε-N-保护炔丙酯合成含氮杂环。
Org Biomol Chem. 2010 Jun 21;8(12):2697-9. doi: 10.1039/c003734f. Epub 2010 Apr 27.
8
Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions.在无溶剂和无酸条件下 Au/Ag 共催化的醛肟到酰胺的重排反应。
J Org Chem. 2010 Feb 19;75(4):1197-202. doi: 10.1021/jo902461a.
9
Gold(I)- and Yb(OTf)(3)-cocatalyzed rearrangements of epoxy alkynes: transfer of a carbonyl group in a five-membered carbocycle.金(I)-和 Yb(OTf)(3)-共催化的环氧炔烃重排:在五元碳环中转移羰基。
Chemistry. 2010 Feb 22;16(8):2496-502. doi: 10.1002/chem.200902321.
10
Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: synthesis of substituted butenolides and isocoumarins.利用亲电路易斯酸性金和路易斯碱性钯进行催化催化:取代丁烯内酯和异香豆素的合成。
J Am Chem Soc. 2009 Dec 23;131(50):18022-3. doi: 10.1021/ja9068497.