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1-氧代-1,3-丁二烯的逆电子需求杂[4+2]环加成反应的最新进展。

Recent Advances in Inverse-Electron-Demand Hetero-Diels-Alder Reactions of 1-Oxa-1,3-Butadienes.

机构信息

Department of Organic Chemistry, Jagiellonian University, Ingardena 3 St, 30-060, Kraków, Poland.

出版信息

Top Curr Chem (Cham). 2016 Jun;374(3):24. doi: 10.1007/s41061-016-0026-2. Epub 2016 Apr 20.

DOI:10.1007/s41061-016-0026-2
PMID:27573264
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5480413/
Abstract

This review is an endeavor to highlight the progress in the inverse-electron-demand hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes in recent years. The huge number of examples of 1-oxadienes cycloadditions found in the literature clearly demonstrates the incessant importance of this transformation in pyran ring synthesis. This type of reaction is today one of the most important methods for the synthesis of dihydropyrans which are the key building blocks in structuring of carbohydrate and other natural products. Two different modes, inter- and intramolecular, of inverse-electron-demand hetero-Diels-Alder reactions of 1-oxadienes are discussed. The domino Knoevenagel hetero-Diels-Alder reactions are also described. In recent years the use of chiral Lewis acids, chiral organocatalysts, new optically active heterodienes or dienophiles have provided enormous progress in asymmetric synthesis. Solvent-free and aqueous hetero-Diels-Alder reactions of 1-oxabutadienes were also investigated. The reactivity of reactants, selectivity of cycloadditions, and chemical stability in aqueous solutions and under physiological conditions were taken into account to show the potential application of the described reactions in bioorthogonal chemistry. New bioorthogonal ligation by click inverse-electron-demand hetero-Diels-Alder cycloaddition of in situ-generated 1-oxa-1,3-butadienes and vinyl ethers was developed. It seems that some of the hetero-Diels-Alder reactions described in this review can be applied in bioorthogonal chemistry because they are selective, non-toxic, and can function in biological conditions taking into account pH, an aqueous environment, and temperature.

摘要

这篇综述旨在强调近年来 1-氧代-1,3-丁二烯的逆电子需求杂 Diels-Alder 反应的研究进展。文献中大量的 1-氧杂二烯环加成实例清楚地表明了这种转化在吡喃环合成中的持续重要性。这种反应是今天合成二氢吡喃的最重要方法之一，二氢吡喃是构建碳水化合物和其他天然产物结构的关键构建块。本文讨论了 1-氧杂二烯的两种不同的逆电子需求杂 Diels-Alder 反应模式：分子内和分子间。还描述了多步 Knoevenagel 杂 Diels-Alder 反应。近年来，手性路易斯酸、手性有机催化剂、新的手性杂二烯或亲二烯体的使用为不对称合成提供了巨大的进展。无溶剂和水相条件下的 1-氧代丁二烯的杂 Diels-Alder 反应也得到了研究。考虑反应物的反应性、环加成的选择性以及在水溶液和生理条件下的化学稳定性，以展示所描述的反应在生物正交化学中的潜在应用。开发了点击逆电子需求杂 Diels-Alder 环加成的新型生物正交连接，该反应由原位生成的 1-氧代-1,3-丁二烯和乙烯基醚引发。由于某些逆电子需求杂 Diels-Alder 反应具有选择性、低毒性，并能在考虑 pH 值、水相环境和温度的情况下在生物条件下发挥作用，因此可以应用于生物正交化学。

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4
Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels-Alder Reactions.交流电电解作为用于异羟肟酸直接电化学氧化以进行酰基亚硝基狄尔斯-阿尔德反应的高效工具。
Angew Chem Int Ed Engl. 2021 Sep 6;60(37):20313-20317. doi: 10.1002/anie.202107148. Epub 2021 Aug 8.
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Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis.金（I）催化的多组分反应合成呋喃并吡喃。
Molecules. 2020 Oct 27;25(21):4976. doi: 10.3390/molecules25214976.
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Novel Synthesis of Substituted 2-Trifluoromethyl and 2-Perfluoroalkyl -Arylpyridinium Compounds-Mechanistic Insights.新型取代 2-三氟甲基和 2-全氟烷基 -芳基吡啶鎓化合物的合成-机理研究。
Molecules. 2019 Jun 25;24(12):2328. doi: 10.3390/molecules24122328.
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Factors Controlling the Diels-Alder Reactivity of Hetero-1,3-Butadienes.控制杂-1,3-丁二烯狄尔斯-阿尔德反应活性的因素。
ChemistryOpen. 2018 Nov 26;7(12):995-1004. doi: 10.1002/open.201800193. eCollection 2018 Dec.
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Covalent modification of biological targets with natural products through Paal-Knorr pyrrole formation.通过帕尔-克诺尔吡咯形成反应利用天然产物对生物靶点进行共价修饰。
Nat Prod Rep. 2017 Aug 30;34(9):1051-1060. doi: 10.1039/c7np00024c.
Synthesis of fused uracils: pyrano[2,3-]pyrimidines and 1,4-bis(pyrano[2,3-]pyrimidinyl)benzenes by domino Knoevenagel/Diels-Alder reactions.
稠合尿嘧啶的合成：通过多米诺Knoevenagel/狄尔斯-阿尔德反应合成吡喃并[2,3 - ]嘧啶和1,4 - 双（吡喃并[2,3 - ]嘧啶基）苯
Monatsh Chem. 2012;143(8):1175-1185. doi: 10.1007/s00706-012-0781-x. Epub 2012 May 24.
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In search of uracil derivatives as bioactive agents. Uracils and fused uracils: Synthesis, biological activity and applications.寻找作为生物活性剂的尿嘧啶衍生物。尿嘧啶及其稠合尿嘧啶：合成、生物活性及应用。
Eur J Med Chem. 2015 Jun 5;97:582-611. doi: 10.1016/j.ejmech.2014.10.008. Epub 2014 Oct 5.
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The asymmetric hetero-Diels-Alder reaction in the syntheses of biologically relevant compounds.不对称杂[2+2]环加成反应在生物相关化合物合成中的应用。
Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11146-57. doi: 10.1002/anie.201404094. Epub 2014 Sep 12.
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Highly enantioselective inverse-electron-demand hetero-Diels-Alder reactions catalyzed by modularly designed organocatalysts.模块化设计的有机催化剂催化的高度对映选择性逆电子需求杂环狄尔斯-阿尔德反应
Chemistry. 2013 May 27;19(22):6976-9. doi: 10.1002/chem.201300168. Epub 2013 Apr 23.
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A bioorthogonal ligation enabled by click cycloaddition of o-quinolinone quinone methide and vinyl thioether.通过邻醌型醌甲基化物与乙烯基硫醚的点击环加成反应实现的生物正交连接。
J Am Chem Soc. 2013 Apr 3;135(13):4996-9. doi: 10.1021/ja401989p. Epub 2013 Mar 25.
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Dienamine-mediated inverse-electron-demand hetero-diels-alder reaction by using an enantioselective H-bond-directing strategy.使用对映选择性氢键导向策略的二烯胺介导的逆电子需求杂 Diels-Alder 反应。
Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13109-13. doi: 10.1002/anie.201207122. Epub 2012 Nov 12.
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Attach, remove, or replace: reversible surface functionalization using thiol-quinone methide photoclick chemistry.附着、去除或替换：使用巯基-醌甲基化物光点击化学进行可逆表面功能化。
J Am Chem Soc. 2012 May 23;134(20):8408-11. doi: 10.1021/ja302970x. Epub 2012 May 14.
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Asymmetric organocatalytic formal [2 + 2]-cycloadditions via bifunctional H-bond directing dienamine catalysis.通过双功能氢键导向烯胺催化的不对称有机催化形式 [2 + 2]-环加成反应。
J Am Chem Soc. 2012 Feb 8;134(5):2543-6. doi: 10.1021/ja211878x. Epub 2012 Jan 27.