• 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

结合常数在通过静电相互作用固定化的手性催化剂效率中的作用:氮杂双(恶唑啉)-铜配合物的情况。

The role of binding constants in the efficiency of chiral catalysts immobilized by electrostatic interactions: the case of azabis(oxazoline)-copper complexes.

作者信息

Fraile José M, García José I, Herrerías Clara I, Mayoral José A, Reiser Oliver, Socuéllamos Antonio, Werner Heiko

机构信息

Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Facultad de Ciencias, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain.

出版信息

Chemistry. 2004 Jun 21;10(12):2997-3005. doi: 10.1002/chem.200305739.

DOI:10.1002/chem.200305739
PMID:15214083
Abstract

As shown by theoretical calculations, azabis(oxazoline)-copper complexes are considerably more stable than the analogous bis(oxazoline)-copper complexes. This enhanced stability allows them to be efficiently immobilized by means of electrostatic interactions to different anionic supports, such as clays and nafion-silica nanocomposites, without the loss of a ligand, as is observed for bis(oxazolines). As a result, enantioselectivities of around 90 % ee are obtained in the cyclopropanation reaction between styrene and ethyl diazoacetate. Moreover, the solid catalyst is easily recoverable.

摘要

理论计算表明,氮杂双(恶唑啉)-铜配合物比类似的双(恶唑啉)-铜配合物稳定得多。这种增强的稳定性使它们能够通过静电相互作用有效地固定在不同的阴离子载体上,如粘土和全氟磺酸-二氧化硅纳米复合材料,而不会像双(恶唑啉)那样损失配体。结果,在苯乙烯与重氮乙酸乙酯的环丙烷化反应中获得了约90%ee的对映选择性。此外,固体催化剂易于回收。

相似文献

1
The role of binding constants in the efficiency of chiral catalysts immobilized by electrostatic interactions: the case of azabis(oxazoline)-copper complexes.结合常数在通过静电相互作用固定化的手性催化剂效率中的作用:氮杂双(恶唑啉)-铜配合物的情况。
Chemistry. 2004 Jun 21;10(12):2997-3005. doi: 10.1002/chem.200305739.
2
A flexible and versatile strategy for the covalent immobilization of chiral catalysts based on pyridinebis(oxazoline) ligands.一种基于吡啶双(恶唑啉)配体的手性催化剂共价固定化的灵活通用策略。
J Org Chem. 2005 Jul 8;70(14):5536-44. doi: 10.1021/jo050504l.
3
On the intermediates in chiral bis(oxazoline)copper(II)-catalyzed enantioselective reactions--experimental and theoretical investigations.手性双(恶唑啉)铜(II)催化对映选择性反应中间体的实验与理论研究
Chemistry. 2002 Apr 15;8(8):1888-98. doi: 10.1002/1521-3765(20020415)8:8<1888::AID-CHEM1888>3.0.CO;2-9.
4
C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions.对映选择性铜-双(恶唑啉)催化环丙烷化反应中C1对称与C2对称配体
Chemistry. 2007;13(31):8830-9. doi: 10.1002/chem.200700681.
5
Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions.共价键合到不溶性载体上的双(恶唑啉)铜配合物作为环丙烷化反应中的催化剂。
J Org Chem. 2001 Dec 28;66(26):8893-901. doi: 10.1021/jo0159338.
6
Enantioselective C-H carbene insertions with homogeneous and immobilized copper complexes.手性铜配合物的均相和固载体系中的 C-H 卡宾插入反应。
Org Biomol Chem. 2011 Sep 7;9(17):6075-81. doi: 10.1039/c1ob05499f. Epub 2011 Jul 13.
7
Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone.具有3,3'-联噻吩骨架的手性双(恶唑啉)配体的空间和电子调谐
J Org Chem. 2005 Sep 16;70(19):7488-95. doi: 10.1021/jo050267m.
8
Synthesis and application of phosphorus dendrimer immobilized azabis(oxazolines).磷树枝状大分子固定化氮杂双(恶唑啉)的合成与应用
Org Lett. 2007 Jul 19;9(15):2895-8. doi: 10.1021/ol071128p. Epub 2007 Jun 29.
9
Polymer-supported Bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions.聚合物负载双(恶唑啉)-铜配合物作为环丙烷化反应中的催化剂。
Org Lett. 2000 Nov 30;2(24):3905-8. doi: 10.1021/ol0066633.
10
Highly enantioselective michael additions of indole to benzylidene malonate using simple bis(oxazoline) ligands: importance of metal/ligand ratio.使用简单的双(恶唑啉)配体实现吲哚对亚苄基丙二酸酯的高度对映选择性迈克尔加成反应:金属/配体比例的重要性。
Org Lett. 2006 Dec 21;8(26):6099-102. doi: 10.1021/ol062697k.

引用本文的文献

1
Chiral amido-oxazoline functionalized MCM-41: A sustainable heterogeneous catalyst for enantioselective Kharasch-Sosnovsky and Henry reactions.手性酰胺-恶唑啉功能化的MCM-41:一种用于对映选择性卡拉施-索斯诺夫斯基反应和亨利反应的可持续多相催化剂。
Heliyon. 2024 Oct 29;10(21):e39911. doi: 10.1016/j.heliyon.2024.e39911. eCollection 2024 Nov 15.
2
Preparation and DFT studies of chiral Cu (I)-complexes of biphenyl bisoxazolines and their application in enantioselective Kharasch-Sosnovsky reaction.联苯双恶唑啉手性铜(I)配合物的制备、密度泛函理论研究及其在对映选择性卡拉施-索斯诺夫斯基反应中的应用
Sci Rep. 2022 Sep 3;12(1):15038. doi: 10.1038/s41598-022-18922-1.
3
Enantioselective Allylic C-H Bond Oxidation of Olefins Using Copper Complexes of Chiral Oxazoline Based Ligands.
手性噁唑啉配体铜配合物对烯烃的对映选择性烯丙位 C-H 键氧化。
Top Curr Chem (Cham). 2022 Mar 10;380(3):20. doi: 10.1007/s41061-022-00375-9.
4
Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts.使用新型可回收的基于恶唑啉的手性多相催化剂合成手性烯丙基酯
ACS Omega. 2020 Aug 24;5(35):22367-22378. doi: 10.1021/acsomega.0c02764. eCollection 2020 Sep 8.
5
Synthesis and Structural Analysis of Palladium(II) Complexes Containing Neutral or Anionic -Symmetric Bis(oxazoline) Ligands: Effects of Substituents in the 5-Position.含中性或阴离子型对称双(恶唑啉)配体的钯(II)配合物的合成与结构分析:5-位取代基的影响
ACS Omega. 2017 Jul 25;2(7):3886-3900. doi: 10.1021/acsomega.7b00457. eCollection 2017 Jul 31.