• 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

使用平面手性[2.2]对环芳烷-咪唑啉N,O-配体的锌催化甲亚胺叶立德的对映选择性[3+2]环加成反应

Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.

作者信息

Kumar Sundaravel Vivek, Guiry Patrick J

机构信息

Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry, University College Dublin (UCD), Belfield, Dublin 4, Ireland.

出版信息

Angew Chem Int Ed Engl. 2022 Aug 15;61(33):e202205516. doi: 10.1002/anie.202205516. Epub 2022 Jun 9.

DOI:10.1002/anie.202205516
PMID:35603757
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9543521/
Abstract

We present a facile synthetic route toward a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligands showed excellent activities in the asymmetric Zn-catalyzed azomethine ylide cycloaddition. Enantioenriched pyrrolidines, in a substrate scope of 20 examples, were accessed in high levels of endo/exo ratios (up to >99/1) and enantioselectivities (up to >99 % ee) with excellent yields (up to 99 %) by using (S,S,S )-UCD-Imphanol/(S,S,R )-UCD-Imphanol, respectively.

摘要

我们展示了一条简便的合成路线，用于制备一系列具有中心手性和平面前手性的新型咪唑啉基-[2.2]对环芳醇（UCD-Imphanol）配体。两组非对映体配体均通过柱色谱成功纯化。该系列配体的初步应用在不对称锌催化的甲亚胺叶立德环加成反应中表现出优异的活性。使用(S,S,S )-UCD-Imphanol/(S,S,R )-UCD-Imphanol分别进行反应，在20个底物范围内可高收率（高达99%）地获得对映体富集的吡咯烷，其endo/exo比例高达>99/1，对映选择性高达>99% ee。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/bb1a1f21152d/ANIE-61-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/d440cce367f4/ANIE-61-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/3c13b37bb457/ANIE-61-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/64c467365321/ANIE-61-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/ac36b436273c/ANIE-61-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/7ac3c277da43/ANIE-61-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/bb1a1f21152d/ANIE-61-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/d440cce367f4/ANIE-61-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/3c13b37bb457/ANIE-61-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/64c467365321/ANIE-61-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/ac36b436273c/ANIE-61-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/7ac3c277da43/ANIE-61-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4d9/9543521/bb1a1f21152d/ANIE-61-0-g002.jpg

相似文献

1
Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.使用平面手性[2.2]对环芳烷-咪唑啉N,O-配体的锌催化甲亚胺叶立德的对映选择性[3+2]环加成反应
Angew Chem Int Ed Engl. 2022 Aug 15;61(33):e202205516. doi: 10.1002/anie.202205516. Epub 2022 Jun 9.
2
Enantioselective Organozinc Addition to Aldehydes Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-Ligands.使用平面手性[2.2]对环芳烷-咪唑啉N,O-配体实现醛的对映选择性有机锌加成反应。
Chemistry. 2024 Dec 23;30(72):e202403345. doi: 10.1002/chem.202403345. Epub 2024 Nov 11.
3
Zn(II)-catalyzed asymmetric [3 + 2] cycloaddition of acyclic enones with azomethine ylides.锌（II）催化的无环烯酮与甲亚胺叶立德的不对称[3+2]环加成反应。
Org Biomol Chem. 2024 Sep 11;22(35):7148-7153. doi: 10.1039/d4ob00854e.
4
New chiral ferrocenyl P,S-ligands for highly diastereo-/enantioselective catalytic [3 + 2] cycloaddition of azomethine ylides with cyclic and acyclic enones.新型手性二茂铁基 P,S-配体用于高非对映选择性/对映选择性催化[3 + 2]环加成反应，其中包括亚胺叶立德与环状和非环状烯酮的反应。
Org Lett. 2010 Dec 3;12(23):5542-5. doi: 10.1021/ol1024647. Epub 2010 Nov 11.
5
Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.银（I）/硫代ClickFerrophos 配合物催化亚胺叶立德与α-烯酮的高区域选择性和对映选择性 1,3-偶极环加成反应。
Org Lett. 2010 Apr 16;12(8):1752-5. doi: 10.1021/ol100336q.
6
Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides.高对映选择性铜（I）-联苯磺磷催化的甲亚胺叶立德的1,3-偶极环加成反应。
J Am Chem Soc. 2005 Nov 30;127(47):16394-5. doi: 10.1021/ja0552186.
7
Catalytic Asymmetric Reactions with -Metallated Azomethine Ylides.手性催化不对称反应与 -金属化亚胺叶立德。
Acc Chem Res. 2020 May 19;53(5):1084-1100. doi: 10.1021/acs.accounts.0c00113. Epub 2020 Apr 22.
8
Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex.铜（I）/ClickFerrophos络合物催化的甲亚胺叶立德的高度对映选择性不对称1,3-偶极环加成反应。
Org Lett. 2008 May 1;10(9):1747-50. doi: 10.1021/ol8003996. Epub 2008 Mar 29.
9
The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides.通过甲亚胺叶立德与α-亚烷基琥珀酰亚胺的1,3-偶极环加成反应，实现铜催化的双螺吡咯烷骨架的不对称构建。
Chem Commun (Camb). 2015 Jun 4;51(44):9212-5. doi: 10.1039/c5cc02362a.
10
Metal Complex-Controlled Regio-, Diastero- and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Benzo[b]thiophene Sulfones.金属配合物控制的甲亚胺叶立德与苯并[b]噻吩砜的区域、非对映和对映选择性1,3-偶极环加成反应
Chemistry. 2018 Feb 21;24(11):2580-2583. doi: 10.1002/chem.201706033. Epub 2018 Jan 29.

引用本文的文献

1
Stereocontrolled Construction of Multi-Chiral [2.2]Paracyclophanes via Cobaltaphotoredox Dual Catalysis.通过钴光氧化还原双催化立体控制构建多手性[2.2]对环芳烷
ACS Catal. 2025 Jun 23;15(13):11716-11725. doi: 10.1021/acscatal.5c03002. eCollection 2025 Jul 4.
2
Tunable Endo/Exo Selectivity in Direct Catalytic Asymmetric 1,3-Dipolar Cycloadditions with Polyfunctional Lewis Acid / Azolium-Aryloxide Catalysts.使用多官能团路易斯酸/氮杂环卡宾-芳氧基催化剂实现直接催化不对称1,3-偶极环加成反应中可调控的内型/外型选择性
Angew Chem Int Ed Engl. 2025 Aug 18;64(34):e202508024. doi: 10.1002/anie.202508024. Epub 2025 Jul 7.
3
One-Step Maleimide-Based Dual Functionalization of Protein N-Termini.

本文引用的文献

1
Zinc-Catalyzed β-Functionalization of Cyclopropanols via Enolized Homoenolate.锌催化的环丙醇β-官能团化：通过烯醇型偕同烯醇盐。
J Am Chem Soc. 2021 Nov 10;143(44):18400-18405. doi: 10.1021/jacs.1c10109. Epub 2021 Oct 29.
2
Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides.镍/光氧化还原催化的苯乙烯氧化物与芳基碘化物的对映选择性交叉电偶联。
J Am Chem Soc. 2021 Sep 29;143(38):15873-15881. doi: 10.1021/jacs.1c08105. Epub 2021 Sep 20.
3
Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds.
基于马来酰亚胺的蛋白质N端一步双重功能化
Angew Chem Int Ed Engl. 2025 Jan 27;64(5):e202417134. doi: 10.1002/anie.202417134. Epub 2024 Nov 27.
4
Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes.有机催化去对称化反应为合成平面手性[2.2]对环芳烷提供了途径。
Nat Commun. 2024 Apr 10;15(1):3090. doi: 10.1038/s41467-024-47407-0.
5
Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic -Ylides and Electron-Deficient Olefins.通过原位生成的杂芳基 -Ylides 和缺电子烯烃的[3 + 2]环加成反应，实现稠合多杂环化合物的多样化合成。
Molecules. 2023 May 29;28(11):4410. doi: 10.3390/molecules28114410.
6
Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.富电子苯并富烯作为甲亚胺叶立德的铜（I）催化不对称1,3-偶极环加成反应中的有效亲偶极体。
Chem Sci. 2023 Apr 25;14(20):5460-5469. doi: 10.1039/d3sc00435j. eCollection 2023 May 24.
吡咯烷在药物发现中的应用：一种新型生物活性化合物的多功能骨架。
Top Curr Chem (Cham). 2021 Aug 10;379(5):34. doi: 10.1007/s41061-021-00347-5.
4
Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.含恶唑啉配体在不对称催化中的进一步发展与应用。
Chem Rev. 2021 Jun 9;121(11):6373-6521. doi: 10.1021/acs.chemrev.0c00844. Epub 2021 May 21.
5
Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam.喹啉：一种新的配体支架可实现镍催化的 α-烷基化 γ-内酰胺的对映选择性合成。
J Am Chem Soc. 2020 Sep 16;142(37):15654-15660. doi: 10.1021/jacs.0c07126. Epub 2020 Sep 1.
6
Lewis-Acid-Catalyzed Asymmetric Alkynylation of Alkynyl 1,2-Diketones: Controllable Formation of 3(2)-Furanones and α-Hydroxy Ketones.Lewis 酸催化的炔基 1,2-二酮不对称炔基化反应：可控合成 3(2)-呋喃酮和α-羟基酮。
Org Lett. 2020 Sep 4;22(17):6948-6953. doi: 10.1021/acs.orglett.0c02505. Epub 2020 Aug 21.
7
Catalytic Asymmetric Reactions with -Metallated Azomethine Ylides.手性催化不对称反应与 -金属化亚胺叶立德。
Acc Chem Res. 2020 May 19;53(5):1084-1100. doi: 10.1021/acs.accounts.0c00113. Epub 2020 Apr 22.
8
Discovery of ABBV/GLPG-3221, a Potent Corrector of CFTR for the Treatment of Cystic Fibrosis.用于治疗囊性纤维化的强效CFTR校正剂ABBV/GLPG-3221的发现。
ACS Med Chem Lett. 2019 Oct 31;10(11):1543-1548. doi: 10.1021/acsmedchemlett.9b00377. eCollection 2019 Nov 14.
9
Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides.通过催化不对称 1,3-偶极环加成反应合成吡咯烷的立体化学多样性。亚胺叶立德。
Chem Commun (Camb). 2019 Oct 3;55(80):11979-11991. doi: 10.1039/c9cc05238k.
10
Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives.[2.2]对环芳烷的区域选择性官能团化：近期合成进展与展望
Angew Chem Int Ed Engl. 2020 Feb 3;59(6):2156-2170. doi: 10.1002/anie.201904863. Epub 2019 Oct 30.