• 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

金催化的炔丙基重氮乙酸酯的1,2-酰氧基迁移/偶联串联反应:异霉素衍生物的合成

Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives.

作者信息

Bao Ming, Wang Xin, Qiu Lihua, Hu Wenhao, Hong Chan Philip Wai, Xu Xinfang

机构信息

School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou , 510006 , China.

College of Chemistry, Chemical Engineering and Materials Science , Soochow University , Suzhou 215123 , China.

出版信息

Org Lett. 2019 Mar 15;21(6):1813-1817. doi: 10.1021/acs.orglett.9b00392. Epub 2019 Mar 6.

DOI:10.1021/acs.orglett.9b00392
PMID:30840467
Abstract

An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.

摘要

已开发出一种高效的金(I)催化的环化反应,用于从炔丙基重氮乙酸酯合成异霉素衍生物。所提出的环化途径描绘了通过金(I)催化的1,2 - 酰氧基迁移原位生成并通过与剩余连接的重氮官能团的交叉偶联反应截获的乙烯基金卡宾物种的第一个实例。质子添加剂的使用对于通过微调金(I)配合物的催化偏好来调节反应结果至关重要。

相似文献

1
Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives.金催化的炔丙基重氮乙酸酯的1,2-酰氧基迁移/偶联串联反应:异霉素衍生物的合成
Org Lett. 2019 Mar 15;21(6):1813-1817. doi: 10.1021/acs.orglett.9b00392. Epub 2019 Mar 6.
2
Gold(I)-Catalyzed and HO-Mediated Carbene Cascade Reaction of Propargyl Diazoacetates: Furan Synthesis and Mechanistic Insights.金(I)催化的偕二氮丙二酸二乙酯与 HO 介导的卡宾级联反应:呋喃合成及机理研究。
Org Lett. 2018 Sep 7;20(17):5332-5335. doi: 10.1021/acs.orglett.8b02251. Epub 2018 Aug 27.
3
Gold-catalyzed carbocyclization and imidization of alkyne-tethered diazo compounds with nitrosoarenes for the synthesis of nitrones and naphthalene derivatives.金催化炔烃键合重氮化合物与亚硝基芳烃的碳环化和酰亚胺化反应合成硝酮和萘衍生物。
Mol Divers. 2023 Oct;27(5):1971-1978. doi: 10.1007/s11030-022-10530-5. Epub 2022 Sep 23.
4
Gold(I)-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition of 1,6-diynes with an ynamide propargyl ester moiety: highly efficient synthesis of functionalized cyclopenta[b]indoles.金(I)催化的1,6-二炔与烯炔丙酯部分的1,2-酰氧基迁移/[3+2]环加成反应:官能化环戊并[b]吲哚的高效合成
Chemistry. 2015 Jan 12;21(3):1009-13. doi: 10.1002/chem.201405965. Epub 2014 Dec 2.
5
Rhodium(II)-catalyzed carbocyclization reaction of alpha-diazo carbonyls with tethered unsaturation.铑(II)催化的α-重氮羰基化合物与相连不饱和键的碳环化反应。
J Org Chem. 2000 Jun 16;65(12):3722-32. doi: 10.1021/jo991938h.
6
A DFT study on the mechanism of gold(III)-catalyzed synthesis of highly substituted furans via [3, 3]-sigmatropic rearrangements and/or [1, 2]-acyloxy migration based on propargyl ketones.基于炔丙基酮的金(III)催化高取代呋喃的[3,3]-σ重排和/或[1,2]-烷氧基迁移合成的密度泛函理论研究。
Org Biomol Chem. 2011 Apr 21;9(8):2760-70. doi: 10.1039/c0ob01098g. Epub 2011 Feb 28.
7
Intramolecular Gold-Catalyzed and NaH-Supported Cyclization Reactions of N-Propargyl Indole Derivatives with Pyrazole and Pyrrole Rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole.N-炔丙基吲哚衍生物与吡唑和吡咯环的分子内金催化及NaH促进的环化反应:吡唑并二氮杂卓吲哚、吡唑并吡嗪吲哚和吡咯并吡嗪吲哚的合成
J Org Chem. 2015 Dec 18;80(24):12552-61. doi: 10.1021/acs.joc.5b02419. Epub 2015 Dec 8.
8
()-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl-Ene Reaction.
Org Lett. 2021 Aug 6;23(15):5669-5673. doi: 10.1021/acs.orglett.1c01782. Epub 2021 Jul 13.
9
A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles.金催化的1,2-酰氧基迁移/分子内环丙烷化/扩环串联反应:中等大小杂环的合成
Chem Commun (Camb). 2015 Sep 21;51(73):13937-40. doi: 10.1039/c5cc05808b.
10
Gold-catalyzed cyclization reactions of allenol and alkynol derivatives.金催化的烯丙醇和炔丙醇衍生物的环化反应。
Acc Chem Res. 2014 Mar 18;47(3):939-52. doi: 10.1021/ar4002558. Epub 2014 Jan 15.

引用本文的文献

1
Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with -Aryl Imines: Synthesis of Tetrahydroquinolines.金催化炔醇与芳基亚胺的氢烷氧基化/波瓦罗夫反应串联:四氢喹啉的合成
ACS Omega. 2019 Sep 9;4(13):15754-15763. doi: 10.1021/acsomega.9b02693. eCollection 2019 Sep 24.