• 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

手性铜催化的自由基过程中烯烃的对映选择性氨基和叠氮氰化反应。

Enantioselective Copper-Catalyzed Intermolecular Amino- and Azidocyanation of Alkenes in a Radical Process.

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.

出版信息

Angew Chem Int Ed Engl. 2017 Feb 13;56(8):2054-2058. doi: 10.1002/anie.201611850. Epub 2017 Jan 23.

DOI:10.1002/anie.201611850
PMID:28111866
Abstract

Asymmetric copper-catalyzed intermolecular amino- and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which a key benzylic radical intermediate is enantioselectively trapped by a chiral Box/Cu cyanide complex. A variety of enantiomerically enriched β-amino/azido alkylnitriles were efficiently synthesized. The β-azido alkylnitriles could be converted into a series of highly valuable optically active amine-based building blocks and bioactive compounds.

摘要

发展了一种不对称铜催化的烯烃分子间的氨基和叠氮氰化反应,该反应通过自由基过程进行,其中关键的苄基自由基中间体被手性 Box/Cu 氰化物络合物对映选择性捕获。多种对映体富集的β-氨基/叠氮烷基腈得到高效合成。β-叠氮烷基腈可以转化为一系列高价值的手性基于胺的构建块和生物活性化合物。

相似文献

1
Enantioselective Copper-Catalyzed Intermolecular Amino- and Azidocyanation of Alkenes in a Radical Process.手性铜催化的自由基过程中烯烃的对映选择性氨基和叠氮氰化反应。
Angew Chem Int Ed Engl. 2017 Feb 13;56(8):2054-2058. doi: 10.1002/anie.201611850. Epub 2017 Jan 23.
2
Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations.铜催化的自由基接力用于不对称自由基转化
Acc Chem Res. 2018 Sep 18;51(9):2036-2046. doi: 10.1021/acs.accounts.8b00265. Epub 2018 Sep 5.
3
Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process.手性铜催化的通过自由基过程的烯烃的对映选择性的氰基三氟甲基化反应。
J Am Chem Soc. 2016 Dec 7;138(48):15547-15550. doi: 10.1021/jacs.6b10468. Epub 2016 Nov 21.
4
Asymmetric Copper-Catalyzed Intermolecular Aminoarylation of Styrenes: Efficient Access to Optical 2,2-Diarylethylamines.不对称铜催化的苯乙烯分子间氨基芳基化反应:高效构建光学 2,2-二芳基乙胺。
J Am Chem Soc. 2017 May 24;139(20):6811-6814. doi: 10.1021/jacs.7b02455. Epub 2017 May 10.
5
Copper-catalyzed intermolecular azidocyanation of aryl alkenes.铜催化的芳基烯烃分子间叠氮氰化反应
Chem Commun (Camb). 2014 Sep 21;50(73):10676-9. doi: 10.1039/c4cc04640d. Epub 2014 Jul 31.
6
Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.通过铜催化的烯烃自由基氧官能化反应实现功能化内酯的通用对映选择性合成。
J Am Chem Soc. 2015 Jul 1;137(25):8069-77. doi: 10.1021/jacs.5b04821. Epub 2015 Jun 23.
7
Copper(I)-Catalyzed Asymmetric Reactions Involving Radicals.铜(I)催化的自由基参与的不对称反应。
Acc Chem Res. 2020 Jan 21;53(1):170-181. doi: 10.1021/acs.accounts.9b00381. Epub 2019 Oct 28.
8
A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper-Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes.抗衡离子/配体调控的铜催化的烯属化合物的化学选择性和对映选择性自由基 1,2-碳酰胺化反应。
J Am Chem Soc. 2022 Oct 5;144(39):18081-18089. doi: 10.1021/jacs.2c08035. Epub 2022 Sep 26.
9
Enantioselective Copper-Catalyzed Alkynylation of Benzylic C-H Bonds via Radical Relay.通过自由基接力实现对苄位 C-H 键的对映选择性铜催化炔基化反应。
J Am Chem Soc. 2020 Jul 15;142(28):12493-12500. doi: 10.1021/jacs.0c05373. Epub 2020 Jun 30.
10
Rhodium-catalyzed enantioselective diboration of simple alkenes.铑催化的简单烯烃对映选择性双硼化反应。
J Am Chem Soc. 2003 Jul 23;125(29):8702-3. doi: 10.1021/ja035851w.

引用本文的文献

1
Transition Metal Catalysis for the Asymmetric Synthesis of 2-Arylethylamines: A Review of the New Millennium.过渡金属催化的2-芳基乙胺不对称合成:新千年综述
Molecules. 2025 Apr 11;30(8):1721. doi: 10.3390/molecules30081721.
2
Copper-Catalyzed Selective Amino-alkoxycarbonylation of Unactivated Alkenes with CO.铜催化未活化烯烃与一氧化碳的选择性氨基烷氧基羰基化反应
J Am Chem Soc. 2025 Feb 26;147(8):6464-6471. doi: 10.1021/jacs.4c13723. Epub 2025 Feb 17.
3
Directed copper-catalyzed C-H functionalization of unactivated olefins with azodicarbonamide compounds.
铜催化未活化烯烃与偶氮二甲酰胺化合物的定向C-H官能化反应
RSC Adv. 2024 Aug 29;14(38):27475-27480. doi: 10.1039/d4ra04113e.
4
Three-Component Radical Cross-Coupling: Asymmetric Vicinal Sulfonyl-Esterification of Alkenes Involving Sulfur Dioxide.三组分自由基交叉偶联:涉及二氧化硫的烯烃的不对称邻位磺酰酯化反应
Adv Sci (Weinh). 2024 Jun;11(23):e2309069. doi: 10.1002/advs.202309069. Epub 2024 Mar 26.
5
Photoexcitation of (diarylmethylene)amino benziodoxolones for alkylamination of styrene derivatives with carboxylic acids.用于使苯乙烯衍生物与羧酸进行烷基化反应的(二芳基亚甲基)氨基苯并碘杂氧酮的光激发作用
Chem Sci. 2023 Dec 12;15(3):1068-1076. doi: 10.1039/d3sc06090j. eCollection 2024 Jan 17.
6
Recent Advances in the Enantioselective Radical Reactions.对映选择性自由基反应的最新进展
Molecules. 2023 Aug 25;28(17):6252. doi: 10.3390/molecules28176252.
7
Enantioselective catalytic radical decarbonylative azidation and cyanation of aldehydes.醛的对映选择性催化自由基脱羰叠氮化和氰化反应。
Sci Adv. 2023 Sep;9(35):eadh5195. doi: 10.1126/sciadv.adh5195. Epub 2023 Sep 1.
8
NHC-catalyzed enantioselective access to β-cyano carboxylic esters via in situ substrate alternation and release.通过原位底物交替和释放实现NHC催化对映选择性合成β-氰基羧酸酯。
Nat Commun. 2023 Aug 12;14(1):4878. doi: 10.1038/s41467-023-40645-8.
9
Cu-catalyzed enantioselective decarboxylative cyanation the synergistic merger of photocatalysis and electrochemistry.铜催化对映选择性脱羧氰化反应:光催化与电化学的协同结合
Chem Sci. 2022 Dec 7;14(3):705-710. doi: 10.1039/d2sc05428k. eCollection 2023 Jan 18.
10
Regioselective Radical Amino-Functionalizations of Allyl Alcohols via Dual Catalytic Cross-Coupling.通过双催化交叉偶联实现烯丙醇的区域选择性自由基氨基官能化
ACS Catal. 2021 Mar 19;11(6):3473-3477. doi: 10.1021/acscatal.1c00404. Epub 2021 Mar 3.