• 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

铑催化末端和内部烯丙醇的环化反应：一种原子经济性和高度对映选择性的构建四氢吡喃的方法。

Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans.

机构信息

Institute for Organic Chemistry, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104, Freiburg im Breisgau, Germany.

出版信息

Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23485-23490. doi: 10.1002/anie.202009166. Epub 2020 Oct 26.

DOI:10.1002/anie.202009166
PMID:32940396
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7756761/
Abstract

A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (-)-centrolobine.

摘要

本文报道了对末端和内部烯丙醇的非对映选择性 Rh 催化环化的综合研究。该方法允许原子经济性和高 syn-选择性地获得合成上重要的 2,4-二取代和 2,4,6-三取代四氢吡喃（THP）。此外，通过良好的官能团相容性和（-）-centrolobine 的对映选择性全合成证明了其实用性和多功能性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/c2d2219c1795/ANIE-59-23485-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/3fc0eaee52fc/ANIE-59-23485-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/656a17924eea/ANIE-59-23485-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/d48625a53a4c/ANIE-59-23485-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/3ef0d5fd11fb/ANIE-59-23485-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/840f00c775b8/ANIE-59-23485-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/c2d2219c1795/ANIE-59-23485-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/3fc0eaee52fc/ANIE-59-23485-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/656a17924eea/ANIE-59-23485-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/d48625a53a4c/ANIE-59-23485-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/3ef0d5fd11fb/ANIE-59-23485-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/840f00c775b8/ANIE-59-23485-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2692/7756761/c2d2219c1795/ANIE-59-23485-g006.jpg

相似文献

1
Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans.铑催化末端和内部烯丙醇的环化反应：一种原子经济性和高度对映选择性的构建四氢吡喃的方法。
Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23485-23490. doi: 10.1002/anie.202009166. Epub 2020 Oct 26.
2
Rhodium-catalyzed diastereoselective synthesis of highly substituted morpholines from nitrogen-tethered allenols.铑催化由氮连接的烯丙醇非对映选择性合成高度取代的吗啉。
Chem Commun (Camb). 2023 Apr 6;59(29):4376-4379. doi: 10.1039/d3cc00151b.
3
Stereoselective synthesis of syn-configured alpha-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids.通过铑催化炔基环氧化物与芳基硼酸的反应合成顺式构型的α-烯醇。
J Org Chem. 2009 Aug 21;74(16):6050-4. doi: 10.1021/jo900987w.
4
Formal [4 + 2] cycloaddition of donor-acceptor cyclobutanes and aldehydes: stereoselective access to substituted tetrahydropyrans.给体-受体环丁烷与醛的形式[4 + 2]环加成反应：立体选择性合成取代四氢吡喃。
J Am Chem Soc. 2009 Oct 14;131(40):14202-3. doi: 10.1021/ja906755e.
5
Diastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via Prins cyclizations of enecarbamates: a formal synthesis of (+)-ratjadone A.通过烯氨基甲酸酯的普林斯环化反应非对映选择性合成2,3,6-三取代四氢吡喃-4-酮：(+)-拉贾酮A的形式合成
J Am Chem Soc. 2004 Oct 6;126(39):12216-7. doi: 10.1021/ja046940r.
6
Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters.铑催化硫代羧酸与末端丙二烯的区域选择性加成：支链烯丙基硫代酯的对映选择性合成。
Chem Commun (Camb). 2022 Feb 3;58(11):1704-1707. doi: 10.1039/d1cc06470c.
7
Rhodium-catalyzed [(3+2)+2] carbocyclization of alkynylidenecyclopropanes with substituted allenes: stereoselective construction of tri- and tetrasubstituted exocyclic olefins.铑催化的取代丙二烯基环丙烷与取代烯丙基的 [(3+2)+2] 碳环化反应：外消旋三取代和四取代烯烃的立体选择性构建。
Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4768-72. doi: 10.1002/anie.201410857. Epub 2015 Feb 27.
8
Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans.铁催化合成C2芳基和N-杂芳基取代的四氢吡喃
J Org Chem. 2015 Dec 18;80(24):12509-25. doi: 10.1021/acs.joc.5b02371. Epub 2015 Nov 25.
9
Atom-economic, regiodivergent, and stereoselective coupling of imidazole derivatives with terminal allenes.原子经济性、区域选择性和立体选择性的咪唑衍生物与末端丙二烯的偶联。
Angew Chem Int Ed Engl. 2014 Feb 17;53(8):2162-5. doi: 10.1002/anie.201309126. Epub 2014 Jan 20.
10
Z-Selective Hydrothiolation of Racemic 1,3-Disubstituted Allenes: An Atom-Economic Rhodium-Catalyzed Dynamic Kinetic Resolution.Z-选择性水合硫氢化消旋 1,3-二取代丙二烯：原子经济性铑催化的动态动力学拆分。
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15818-22. doi: 10.1002/anie.201507623. Epub 2015 Sep 29.

引用本文的文献

1
Substrate NOBINAc ligand affinity for Pd-catalyzed enantioselective C-H activation over reactive β-C-H bonds in ferrocenyl amines.在二茂铁胺中，底物NOBINAc配体对钯催化的对映选择性C-H活化反应中活性β-C-H键的亲和力。
Chem Sci. 2024 Dec 13;16(2):700-708. doi: 10.1039/d4sc06867j. eCollection 2025 Jan 2.
2
Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes.通过铑催化的丙二烯和炔烃直接氢磺酰化反应对映选择性合成烯丙基砜
J Am Chem Soc. 2024 Jun 26;146(25):16996-17002. doi: 10.1021/jacs.4c05629. Epub 2024 Jun 14.
3
Catalytic asymmetric oxa-Diels-Alder reaction of acroleins with simple alkenes.

本文引用的文献

1
Rhodium-Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3-Diketones.铑催化外消旋内联烯向对映体纯烯丙基1,3-二酮的平行动力学拆分
Angew Chem Int Ed Engl. 2019 Jul 15;58(29):9939-9943. doi: 10.1002/anie.201903365. Epub 2019 Jun 6.
2
Transition metal catalyzed stereodivergent synthesis of - and -δ-vinyl-lactams: formal total synthesis of (-)-cermizine C and (-)-senepodine G.过渡金属催化的α-和δ-乙烯基内酰胺的立体发散合成：（-）-西米嗪C和（-）-塞内波定G的形式全合成
Chem Sci. 2019 Jan 24;10(10):3074-3079. doi: 10.1039/c8sc05502e. eCollection 2019 Mar 14.
3
Concise Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C -Symmetric Dimerization Strategy.
简单烯烃与丙烯醛的催化不对称氧化 Diels-Alder 反应。
Nat Commun. 2023 Jun 14;14(1):3511. doi: 10.1038/s41467-023-39184-z.
4
Enantioselective Hydroalkoxylation of 1,3-Dienes via Ni-Catalysis.通过镍催化实现1,3 - 二烯的对映选择性氢烷氧基化反应。
J Am Chem Soc. 2023 Feb 10;145(7):3909-14. doi: 10.1021/jacs.2c12779.
5
Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.C-C 多重键的催化不对称羟烷化反应。
Chem Rev. 2021 Dec 22;121(24):14649-14681. doi: 10.1021/acs.chemrev.1c00620. Epub 2021 Dec 3.
6
Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes.通过对炔烃和烯丙基的对映选择性铑催化氢官能化反应，得到对映体富集的α-乙烯基 1,4-苯并二氮杂䓬和 1,4-苯并恶嗪。
J Org Chem. 2021 Aug 6;86(15):10889-10902. doi: 10.1021/acs.joc.1c01268. Epub 2021 Jul 14.
7
Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.解读烯丙醇的多变化学性质：打破曾经神秘官能团的禁忌
Chem Rev. 2021 Apr 14;121(7):4193-4252. doi: 10.1021/acs.chemrev.0c00986. Epub 2021 Feb 25.
通过铑催化的 C 对称二聚化策略简洁地全合成 (-)- Vermiculine。
Chemistry. 2019 Mar 7;25(14):3532-3535. doi: 10.1002/chem.201900216. Epub 2019 Feb 12.
4
Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles.钯和铑催化外消旋内烯的动态动力学拆分制备手性吡唑。
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3378-3381. doi: 10.1002/anie.201812984. Epub 2019 Jan 29.
5
Total Synthesis of (-)-Cylindrocyclophane F: A Yardstick for Probing New Catalytic C-C Bond-Forming Methodologies.(-)-Cylindrocyclophane F 的全合成：探索新型催化 C-C 键形成方法的基准。
Chemistry. 2018 Nov 13;24(63):16770-16773. doi: 10.1002/chem.201804585. Epub 2018 Oct 22.
6
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C -Symmetric Macrodiolides.铑催化的ω-联烯基羧酸对映选择性二聚反应：C-对称大环双内酯的简便合成
Angew Chem Int Ed Engl. 2018 May 28;57(22):6572-6576. doi: 10.1002/anie.201803369. Epub 2018 May 3.
7
Rhodium-Catalyzed Enantioselective Decarboxylative Alkynylation of Allenes with Arylpropiolic Acids.铑催化的对映选择性脱羧炔基化烯丙基与芳基丙二腈。
Org Lett. 2018 Feb 16;20(4):1066-1069. doi: 10.1021/acs.orglett.7b04035. Epub 2018 Feb 5.
8
Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes.铑催化的三唑与内部炔烃和末端烯丙基的区域、对映选择性烯丙基化反应。
Org Lett. 2018 Feb 2;20(3):598-601. doi: 10.1021/acs.orglett.7b03708. Epub 2018 Jan 19.
9
Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans.金（I）催化的丙二烯酰胺、烯烃和醛的[2 + 2 + 2]环加成反应：一种合成四氢吡喃的直接方法。
Chem Sci. 2015 May 1;6(5):2903-2908. doi: 10.1039/c5sc00295h. Epub 2015 Mar 2.
10
Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones.过渡金属催化的区域发散性和立体选择性合成支链和直链烯丙基化4-吡啶酮
Chemistry. 2017 May 11;23(27):6531-6534. doi: 10.1002/chem.201701382. Epub 2017 Apr 13.