• 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

铜/硼酸双催化对多元醇的对映选择性丙炔化和内消旋 1,2-二醇的去对称化。

Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis.

机构信息

Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041, China.

Department of Chemistry, Yale University, New Haven, CT, 06520-8107, USA.

出版信息

Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7213-7217. doi: 10.1002/anie.201703029. Epub 2017 May 19.

DOI:10.1002/anie.201703029
PMID:28523904
Abstract

A copper/borinic acid dual catalytic reaction enabled the enantioselective propargylation of aliphatic polyols. Readily available reagents and catalysts were used in this transformation, which displayed good to excellent chemo- and stereoselectivity for a broad array of substrates. The method was also applicable to the desymmetrization of meso 1,2-diols to furnish products with three stereogenic centers and a terminal alkyne group in one operation.

摘要

铜/硼酸双催化反应实现了脂肪族多元醇的对映选择性炔丙基化反应。该转化使用了易得的试剂和催化剂,对广泛的底物表现出良好到优秀的化学和立体选择性。该方法也适用于外消旋 1,2-二醇的去对称化,以在一步反应中得到具有三个手性中心和末端炔基的产物。

相似文献

1
Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis.铜/硼酸双催化对多元醇的对映选择性丙炔化和内消旋 1,2-二醇的去对称化。
Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7213-7217. doi: 10.1002/anie.201703029. Epub 2017 May 19.
2
Enantioselective enzymatic desymmetrization of highly functionalized meso tetrahydropyranyl diols.高官能化内消旋四氢吡喃二醇的对映选择性酶促去对称化反应
Org Lett. 2009 Nov 5;11(21):4950-3. doi: 10.1021/ol902107g.
3
Diastereo- and Enantioselective Propargylation of 5H-Thiazol-4-ones and 5H-Oxazol-4-ones as Enabled by Cu/Zn and Cu/Ti Catalysis.铜/锌和铜/钛催化实现的5H-噻唑-4-酮和5H-恶唑-4-酮的非对映和对映选择性炔丙基化反应
Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15217-15221. doi: 10.1002/anie.201809391. Epub 2018 Oct 24.
4
Desymmetrization of meso-bisphosphates using copper catalysis and alkylzirconocene nucleophiles.使用铜催化和烷基锆烯亲核试剂对介-双膦酸盐进行去对称化。
Nat Commun. 2019 Jan 3;10(1):21. doi: 10.1038/s41467-018-07871-x.
5
Synthesis of a -Symmetric Chiral Borinic Acid and Its Application in Catalytic Desymmetrization of 2,2-Disubstituted-1,3-Propanediols.α-对称手性硼酸的合成及其在2,2-二取代-1,3-丙二醇催化去对称化反应中的应用。
J Am Chem Soc. 2023 Apr 10. doi: 10.1021/jacs.3c02331.
6
Highly Enantioselective Acylation of Acyclic Meso 1,3-Diols through Synergistic Isothiourea-Catalyzed Desymmetrization/Chiroablative Kinetic Resolution.通过协同异硫脲催化的去对称化/手性消融动力学拆分实现无环内消旋1,3 -二醇的高度对映选择性酰化反应。
Org Lett. 2015 May 1;17(9):2118-21. doi: 10.1021/acs.orglett.5b00707. Epub 2015 Apr 13.
7
Copper ion-induced activation and asymmetric benzoylation of 1,2-diols: kinetic chiral molecular recognition.铜离子诱导的1,2 -二醇的活化及不对称苯甲酰化反应:动力学手性分子识别
J Am Chem Soc. 2003 Feb 26;125(8):2052-3. doi: 10.1021/ja0289402.
8
Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides. lzhao@diversa.com.环氧水解酶催化内消旋环氧化合物去对称化对映选择性合成手性1,2 -二醇。lzhao@diversa.com。
J Am Chem Soc. 2004 Sep 15;126(36):11156-7. doi: 10.1021/ja0466210.
9
Asymmetric desymmetrization based on an intramolecular haloetherification: a highly effective and recyclable chiral nonracemic auxiliary, 2-exo-methyl-3-endo-phenyl-5-norbornene-2-carboxaldehyde, for meso-1,3- and meso-1,4-diols.基于分子内卤代醚化的不对称去对称化反应:一种用于内消旋-1,3-二醇和内消旋-1,4-二醇的高效且可循环使用的手性非外消旋辅助剂,即2-外向-甲基-3-内向-苯基-5-降冰片烯-2-甲醛。
Chemistry. 2004 Oct 25;10(21):5386-97. doi: 10.1002/chem.200400444.
10
Axially Chiral Borinic Acid Catalysts: Design, Synthesis, and Application in Alkylative Desymmetrization of 1,2-Diols.轴手性硼酸催化剂:1,2 - 二醇烷基化去对称化反应中的设计、合成与应用
J Org Chem. 2023 Oct 6;88(19):14178-14183. doi: 10.1021/acs.joc.3c01143. Epub 2023 Sep 16.

引用本文的文献

1
Enantioselective construction of cyclic quaternary stereocenters via dinuclear copper catalyzed asymmetric [3 + 2] propargylation/annulation.通过双核铜催化的不对称[3+2]炔丙基化/环化反应对环状季碳立体中心进行对映选择性构建。
Nat Commun. 2025 Aug 5;16(1):7191. doi: 10.1038/s41467-025-62564-6.
2
Copper-catalyzed yne-allylic substitutions: concept and recent developments.铜催化的炔烃-烯丙基取代反应:概念与最新进展
Beilstein J Org Chem. 2024 Oct 31;20:2739-2775. doi: 10.3762/bjoc.20.232. eCollection 2024.
3
Metal-Catalyzed Enantioconvergent Transformations.
金属催化的对映汇聚转化
Chem Rev. 2023 Oct 25;123(20):11817-11893. doi: 10.1021/acs.chemrev.3c00059. Epub 2023 Oct 4.
4
Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.炔丙基衍生物的合成进展及其作为合成中间体和构建块的应用。
Molecules. 2023 Apr 11;28(8):3379. doi: 10.3390/molecules28083379.
5
Copper-catalysed enantioconvergent alkylation of oxygen nucleophiles.铜催化的对映选择性亲核烷基化反应。
Nature. 2023 Jun;618(7964):301-307. doi: 10.1038/s41586-023-06001-y. Epub 2023 Mar 30.
6
Copper-Catalyzed Asymmetric Sulfonylative Desymmetrization of Glycerol.铜催化的甘油不对称砜基化去对称化反应。
Molecules. 2022 Dec 18;27(24):9025. doi: 10.3390/molecules27249025.
7
Emergent Organoboron Acid Catalysts.新型有机硼酸催化剂
J Org Chem. 2024 Feb 16;89(4):2069-2089. doi: 10.1021/acs.joc.2c01695. Epub 2022 Nov 14.
8
Stereoselective synthesis of C3-tetrasubstituted oxindoles copper catalyzed asymmetric propargylation.C3-四取代氧化吲哚的立体选择性合成:铜催化不对称炔丙基化反应
RSC Adv. 2022 Sep 21;12(41):26727-26732. doi: 10.1039/d2ra04603b. eCollection 2022 Sep 16.
9
Effect of Propargylic Substituents on Enantioselectivity and Reactivity in Ruthenium-Catalyzed Propargylic Substitution Reactions: A DFT Study.炔丙基取代基对钌催化炔丙基取代反应中对映选择性和反应活性的影响:一项密度泛函理论研究
ACS Omega. 2022 Oct 4;7(41):36634-36642. doi: 10.1021/acsomega.2c04645. eCollection 2022 Oct 18.
10
Scope and advances in the catalytic propargylic substitution reaction.催化炔丙基取代反应的范围与进展
RSC Adv. 2018 Sep 5;8(54):31129-31193. doi: 10.1039/c8ra04481c. eCollection 2018 Aug 30.