• 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

通过催化烯基到烯丙基 1,4-铑（I）迁移实现酮与 1,3-烯炔的芳基化分子内烯丙基化反应。

Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

机构信息

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK.

出版信息

Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7227-7232. doi: 10.1002/anie.201703155. Epub 2017 May 19.

DOI:10.1002/anie.201703155
PMID:28523779
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5488243/
Abstract

Alkenyl-to-allyl 1,4-rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C-H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3-enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur-alkene ligand.

摘要

烯基到烯丙基 1,4-铑（I）迁移通过远程 C-H 活化生成亲核烯丙基铑（I）物种。这种新的反应模式被用于含酮的 1,3-炔基桥联底物与芳基硼试剂的非对映选择性反应，得到含有三个连续立体中心的产物。使用手性硫-烯配体可以获得高对映选择性的产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/38c171c1bb78/ANIE-56-7227-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/5c7efed7b71c/ANIE-56-7227-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/a7985fc66293/ANIE-56-7227-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/401b8d8514c7/ANIE-56-7227-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/0be5ecf1f0d2/ANIE-56-7227-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/38c171c1bb78/ANIE-56-7227-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/5c7efed7b71c/ANIE-56-7227-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/a7985fc66293/ANIE-56-7227-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/401b8d8514c7/ANIE-56-7227-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/0be5ecf1f0d2/ANIE-56-7227-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a04/5488243/38c171c1bb78/ANIE-56-7227-g005.jpg

相似文献

1
Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.通过催化烯基到烯丙基 1,4-铑（I）迁移实现酮与 1,3-烯炔的芳基化分子内烯丙基化反应。
Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7227-7232. doi: 10.1002/anie.201703155. Epub 2017 May 19.
2
One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration.通过催化C-H官能化和1,4-铑（III）迁移实现1,3-烯炔的单碳氧化环化反应
Chemistry. 2018 Mar 15;24(16):4050-4054. doi: 10.1002/chem.201706043. Epub 2018 Feb 21.
3
Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.手性铑催化的芳基硼酸、1,3-烯炔和亚胺的对映选择性偶联反应：通过烯基到烯丙基 1,4-铑（I）迁移。
Angew Chem Int Ed Engl. 2017 Dec 18;56(51):16352-16356. doi: 10.1002/anie.201709334. Epub 2017 Nov 24.
4
The isomerization of allylrhodium intermediates in the rhodium-catalyzed nucleophilic allylation of cyclic imines.铑催化环状亚胺的亲核烯丙基化反应中烯丙基铑中间体的异构化
Angew Chem Int Ed Engl. 2014 Oct 20;53(43):11605-10. doi: 10.1002/anie.201407233. Epub 2014 Sep 9.
5
Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes.铑催化的炔烃偕碳金属化引发的1,5-烯炔的芳基化和烯基化环化反应
J Am Chem Soc. 2006 Dec 13;128(49):15598-9. doi: 10.1021/ja067125+.
6
Asymmetric Synthesis of Alkylzincs by Rhodium-Catalyzed Enantioselective Arylative Cyclization of 1,6-Enynes with Arylzincs.铑催化1,6-烯炔与芳基锌的对映选择性芳基化环化反应不对称合成烷基锌
Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18510-18514. doi: 10.1002/anie.202008770. Epub 2020 Aug 18.
7
Rhodium(III)-Catalyzed Asymmetric [4+1] and [5+1] Annulation of Arenes and 1,3-Enynes: A Distinct Mechanism of Allyl Formation and Allyl Functionalization.铑(III)催化芳基和 1,3-烯炔的不对称[4+1]和[5+1]环加成：烯丙基形成和烯丙基官能化的独特机理。
Angew Chem Int Ed Engl. 2020 Dec 7;59(50):22706-22713. doi: 10.1002/anie.202010832. Epub 2020 Oct 7.
8
Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.铑催化亚胺的亲核烯丙基化反应中烯丙基铑物种向酯的链行走
Angew Chem Int Ed Engl. 2016 Jan 18;55(3):1108-12. doi: 10.1002/anie.201508964. Epub 2015 Dec 3.
9
Catalytic asymmetric synthesis of allylsilanes through rhodium/chiral diene-catalyzed 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes.通过铑/手性二烯催化的烯基[2-(羟甲基)苯基]二甲基硅烷的1,4-加成反应实现烯丙基硅烷的催化不对称合成。
Org Lett. 2007 Oct 25;9(22):4643-5. doi: 10.1021/ol702125q. Epub 2007 Oct 3.
10
All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration.铑（III）催化的C-H官能化和1,4-迁移实现1,3-烯炔的全碳[3+3]氧化环化反应
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):9958-62. doi: 10.1002/anie.201503978. Epub 2015 Jul 15.

引用本文的文献

1
Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.镍催化的炔烃和丙二烯醚亲电试剂的芳基化环化反应使用芳基硼试剂。
Chemistry. 2022 Mar 28;28(18):e202104230. doi: 10.1002/chem.202104230. Epub 2022 Jan 27.
2
Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration.通过1,4-铑（I）迁移实现炔基1,3-二酮的催化对映选择性芳基化环化反应。
Chem Sci. 2020 Feb 6;11(10):2759-2764. doi: 10.1039/c9sc06309a.
3
Rhodium(iii)-catalyzed diverse [4 + 1] annulation of arenes with 1,3-enynes sp/sp C-H activation and 1,4-rhodium migration.

本文引用的文献

1
Cobalt-Catalyzed Allylic C(sp)-H Carboxylation with CO.钴催化的与 CO 的烯丙基 C(sp)-H 羧化反应。
J Am Chem Soc. 2017 May 3;139(17):6094-6097. doi: 10.1021/jacs.7b02775. Epub 2017 Apr 20.
2
Copper(I)-Catalyzed Enantioselective Addition of Enynes to Ketones.铜（I）催化的炔烃对酮的对映选择性加成。
J Am Chem Soc. 2017 Apr 5;139(13):4647-4650. doi: 10.1021/jacs.7b01254. Epub 2017 Mar 21.
3
Formal Allylic C(sp)-H Bond Activation of Alkenes Triggered by a Sodium Amide.酰胺引发的烯烃的偕 C(sp 2 )-H 键的形式化亲核活化
铑（III）催化芳烃与1,3-烯炔的多样[4 + 1]环化反应：sp/sp C-H活化和1,4-铑迁移
Chem Sci. 2019 Feb 26;10(14):3987-3993. doi: 10.1039/c9sc00545e. eCollection 2019 Apr 14.
4
Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.手性铑催化的芳基硼酸、1,3-烯炔和亚胺的对映选择性偶联反应：通过烯基到烯丙基 1,4-铑（I）迁移。
Angew Chem Int Ed Engl. 2017 Dec 18;56(51):16352-16356. doi: 10.1002/anie.201709334. Epub 2017 Nov 24.
5
Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process.通过光驱动的有机催化Aldol 去对称化过程来形成含氟季立体中心。
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11875-11879. doi: 10.1002/anie.201706763. Epub 2017 Aug 18.
J Am Chem Soc. 2017 Mar 29;139(12):4362-4365. doi: 10.1021/jacs.7b01542. Epub 2017 Mar 20.
4
Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.铜催化的亚胺、丙二烯和二硼烷的三组分偶联反应中立体中心的对映选择性生成。
Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11912-6. doi: 10.1002/anie.201606710. Epub 2016 Aug 19.
5
Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.对映选择性醇 C-H 功能化在聚酮构建中的应用：为理想化学合成解锁氧化还原经济性和位点选择性。
J Am Chem Soc. 2016 May 4;138(17):5467-78. doi: 10.1021/jacs.6b02019. Epub 2016 Apr 26.
6
Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.铑催化亚胺的亲核烯丙基化反应中烯丙基铑物种向酯的链行走
Angew Chem Int Ed Engl. 2016 Jan 18;55(3):1108-12. doi: 10.1002/anie.201508964. Epub 2015 Dec 3.
7
Iridium-Catalyzed C-C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (Z)-Siloxyallylation.铱催化简单炔丙基醚与伯醇的C-C偶联：通过氧化还原引发的(Z)-硅氧基烯丙基化实现对映选择性高烯丙基醇加成反应
J Am Chem Soc. 2015 Dec 30;137(51):16024-7. doi: 10.1021/jacs.5b12131. Epub 2015 Dec 15.
8
Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.钌催化的炔丙基醚与醇的非对映和对映选择性偶联：通过氢化物迁移实现的硅氧基巴豆酰化反应将炔烃转化为π-烯丙基。
J Am Chem Soc. 2015 Oct 14;137(40):13066-71. doi: 10.1021/jacs.5b08019. Epub 2015 Sep 29.
9
Asymmetric Allylic C-H Oxidation for the Synthesis of Chromans.不对称烯丙位 C-H 氧化反应在色满合成中的应用。
J Am Chem Soc. 2015 Oct 14;137(40):12732-5. doi: 10.1021/jacs.5b08477. Epub 2015 Oct 1.
10
All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration.铑（III）催化的C-H官能化和1,4-迁移实现1,3-烯炔的全碳[3+3]氧化环化反应
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):9958-62. doi: 10.1002/anie.201503978. Epub 2015 Jul 15.