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作为反应平台的分级组装螺旋配合物——从化学计量的狄尔斯-阿尔德反应到烯胺催化

Hierarchically assembled helicates as reaction platform - from stoichiometric Diels-Alder reactions to enamine catalysis.

作者信息

Van Craen David, Begall Jenny, Großkurth Johannes, Himmel Leonard, Linnenberg Oliver, Isaak Elisabeth, Albrecht Markus

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.

出版信息

Beilstein J Org Chem. 2020 Sep 24;16:2338-2345. doi: 10.3762/bjoc.16.195. eCollection 2020.

DOI:10.3762/bjoc.16.195
PMID:33029252
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7522461/
Abstract

The stereoselectivity of a Diels-Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands was investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile were carefully varied. Based on the results of the stoichiometric reaction, a secondary amine-catalyzed nitro-Michael reaction is performed as well which afforded reasonable diastereoselectivities.

摘要

详细研究了由非手性、反应性配体与手性、非反应性配体混合物形成的分级组装钛（IV）螺旋体周边内狄尔斯-阿尔德反应的立体选择性。沿着手性诱导途径，对手性配体、溶剂以及亲双烯体上的取代基进行了仔细的变化。基于化学计量反应的结果，还进行了仲胺催化的硝基迈克尔反应，该反应提供了合理的非对映选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/27896f2e8c2f/Beilstein_J_Org_Chem-16-2338-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/5bea655d90a5/Beilstein_J_Org_Chem-16-2338-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/65d2a832906b/Beilstein_J_Org_Chem-16-2338-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/fa739d56280c/Beilstein_J_Org_Chem-16-2338-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/27896f2e8c2f/Beilstein_J_Org_Chem-16-2338-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/5bea655d90a5/Beilstein_J_Org_Chem-16-2338-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/65d2a832906b/Beilstein_J_Org_Chem-16-2338-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/fa739d56280c/Beilstein_J_Org_Chem-16-2338-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d85e/7522461/27896f2e8c2f/Beilstein_J_Org_Chem-16-2338-g005.jpg

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本文引用的文献

1
Catalytic reactions within the cavity of coordination cages.配位笼腔内的催化反应。
Chem Soc Rev. 2019 Aug 27;48(17):4707-4730. doi: 10.1039/c9cs00091g.
2
Chasing Weak Forces: Hierarchically Assembled Helicates as a Probe for the Evaluation of the Energetics of Weak Interactions.追逐弱力：作为评估弱相互作用能量的探针的分级组装螺旋。
J Am Chem Soc. 2017 Nov 22;139(46):16959-16966. doi: 10.1021/jacs.7b10098. Epub 2017 Nov 8.
3
A Supramolecular Chiral Auxiliary Approach: "Remote Control" of Stereochemistry at a Hierarchically Assembled Dimeric Helicate.
一种超分子手性助剂方法：在分层组装的二聚体螺旋配合物中对立体化学的“远程控制” 。
Chemistry. 2016 Mar 1;22(10):3255-3258. doi: 10.1002/chem.201600158. Epub 2016 Feb 2.
4
Nucleophilic substitution catalyzed by a supramolecular cavity proceeds with retention of absolute stereochemistry.超分子空腔催化的亲核取代反应具有立体化学的绝对构型保持。
J Am Chem Soc. 2014 Oct 15;136(41):14409-12. doi: 10.1021/ja508799p. Epub 2014 Oct 7.
5
Terpenols as substituents for the diastereoselective formation of enantiomerically pure triple lithium-bridged helicate type-coordination compounds.萜烯醇作为对映体纯的三锂桥连螺旋型配位化合物非对映选择性形成的取代基。
Dalton Trans. 2014 Oct 21;43(39):14636-43. doi: 10.1039/c4dt01553c.
6
Side arm strategy for catalyst design: modifying bisoxazolines for remote control of enantioselection and related.侧臂策略在催化剂设计中的应用：双恶唑啉的修饰对远程控制对映选择性及相关的研究
Acc Chem Res. 2014 Aug 19;47(8):2260-72. doi: 10.1021/ar800104y. Epub 2014 May 16.
7
Stereocontrol in dinuclear triple lithium-bridged titanium(IV) complexes: solving some stereochemical mysteries.双核三锂桥联钛（IV）配合物中的立体化学控制：解开一些立体化学谜团。
Chemistry. 2014 May 26;20(22):6650-8. doi: 10.1002/chem.201402370. Epub 2014 Apr 29.
8
Synthesis, pH-dependent, and plasma stability of meropenem prodrugs for potential use against drug-resistant tuberculosis.合成、pH 依赖性和替莫培南前药的血浆稳定性，用于潜在治疗耐药性结核病。
Bioorg Med Chem. 2013 Sep 1;21(17):5605-17. doi: 10.1016/j.bmc.2013.05.024. Epub 2013 May 24.
9
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