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协同路易斯酸/杂环卡宾催化

Cooperative Lewis acid/-heterocyclic carbene catalysis.

作者信息

Cohen Daniel T, Scheidt Karl A

机构信息

Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL, 60208, USA.

出版信息

Chem Sci. 2012 Jan 1;3(1):53-57. doi: 10.1039/C1SC00621E.

DOI:10.1039/C1SC00621E
PMID:26413259
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4583212/
Abstract

Lewis acid activation with -heterocyclic carbene (NHC) catalysis has presented new opportunities for enantioselective reaction development. Recent findings illustrate that Lewis acids can play an important role in homoenolate annulations by: enhancement of the reactivity, reversal of the diastereo- or regioselectivity, and activation of previously inactive electrophiles. Additionally, the incorporation of a Lewis acid into Brønsted base-catalyzed conjugate addition allowed for an increase in yields.

摘要

用氮杂环卡宾(NHC)催化进行路易斯酸活化,为对映选择性反应的发展带来了新机遇。最近的研究结果表明,路易斯酸可通过以下方式在同烯醇化物环化反应中发挥重要作用:提高反应活性、反转非对映或区域选择性以及活化先前无活性的亲电试剂。此外,将路易斯酸引入布朗斯特碱催化的共轭加成反应中可提高产率。

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本文引用的文献

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The effect of the -mesityl group in NHC-catalyzed reactions.N-杂环卡宾催化反应中 - 均三甲苯基的作用。
Chem Sci. 2012 Jan 1;3(1):192-197. doi: 10.1039/C1SC00397F.
2
Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes.由氮杂环卡宾生成的高烯醇负离子类似物的质子化反应。
Synthesis (Stuttg). 2008 Apr;2008(8):1306-1315. doi: 10.1055/s-2008-1072516.
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Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.烯胺/卡宾串联催化用于功能化环戊酮的非对映和对映选择性合成
Chem Sci. 2011 Sep 1;2(9):1835-1838. doi: 10.1039/C1SC00175B.
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Organocatalytic iminium ion/carbene reaction cascade for the formation of optically active 2,4-disubstituted cyclopentenones.有机催化亚胺离子/卡宾反应级联反应用于构建光学活性 2,4-二取代环戊烯酮。
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Understanding the cooperative NHC/LA catalysis for stereoselective annulation reactions with homoenolates. A DFT study.理解 NHC/LA 协同催化的高烯醇酯立体选择性环化反应。DFT 研究。
Org Biomol Chem. 2011 Oct 7;9(19):6616-22. doi: 10.1039/c1ob05609c. Epub 2011 Aug 15.
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Highly diastereo- and enantioselective NHC-catalyzed [3+2] annulation of enals and isatins.高非对映选择性和对映选择性的 NHC 催化烯醛和靛红的 [3+2] 环加成反应。
Chem Commun (Camb). 2011 Sep 28;47(36):10136-8. doi: 10.1039/c1cc13860j. Epub 2011 Aug 9.
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N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.N-杂环卡宾和布朗斯特酸协同催化:反式γ-内酰胺的不对称合成。
J Am Chem Soc. 2011 Aug 17;133(32):12466-9. doi: 10.1021/ja205714g. Epub 2011 Jul 25.
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