将吡咯烷和哌啶氧化以得到具有碳氢官能化的异丙基-1-羧酸酯类似物。
Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.
作者信息
Gunawan Steven, Bedard Nathan, Foley Christopher, Hulme Christopher
机构信息
Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, United States.
Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona, Tucson, AZ 85737, United States.
出版信息
Tetrahedron Lett. 2021 Apr 13;69. doi: 10.1016/j.tetlet.2021.152978. Epub 2021 Mar 17.
Abstract
This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc), and iodosobenzene, (PhIO)] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected -heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.
摘要
本文描述了碘（III）试剂[二乙酰氧基碘苯，PhI(OAc)₂，和亚碘酰苯，(PhIO)]与TMSBr协同作用，在饱和、氨基甲酸酯保护的杂环独特氧化反应中充当功能性溴等价物的情况。有趣的是，在这项工作中，仅用分子溴处理相同的氨基甲酸酯得到了类似的产物，这些产物被溶剂甲醇分离。
相似文献
1
Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners.将吡咯烷和哌啶氧化以得到具有碳氢官能化的异丙基-1-羧酸酯类似物。
Tetrahedron Lett. 2021 Apr 13;69. doi: 10.1016/j.tetlet.2021.152978. Epub 2021 Mar 17.
2
Iodine(III) Reagents in Radical Chemistry.碘(III)试剂在自由基化学中的应用。
Acc Chem Res. 2017 Jul 18;50(7):1712-1724. doi: 10.1021/acs.accounts.7b00148. Epub 2017 Jun 21.
3
Convenient syntheses of fluorous aryl iodides and hypervalent iodine compounds: ArI(L)n reagents that are recoverable by simple liquid/liquid biphase workups, and applications in oxidations of hydroquinones.氟代芳基碘化物和高价碘化合物的简便合成：可通过简单液/液双相后处理回收的ArI(L)n试剂及其在对苯二酚氧化反应中的应用
Chemistry. 2003 Jan 3;9(1):88-95. doi: 10.1002/chem.200390034.
4
Hypervalent iodine reagent mediated reaction of [60]fullerene with amines.高价碘试剂介导的[60]富勒烯与胺的反应。
J Org Chem. 2013 Dec 6;78(23):12257-62. doi: 10.1021/jo402079m. Epub 2013 Nov 21.
5
Direct cyanation of heteroaromatic compounds mediated by hypervalent iodine(III) reagents: In situ generation of PhI(III)-CN species and their cyano transfer.高价碘（III）试剂介导的杂环芳烃的直接氰化反应：PhI(III)-CN物种的原位生成及其氰基转移
J Org Chem. 2007 Jan 5;72(1):109-16. doi: 10.1021/jo061820i.
6
Hypervalent iodine-guided electrophilic substitution: -selective substitution across aryl iodonium compounds with benzyl groups.高价碘导向的亲电取代反应：通过苄基对芳基碘鎓化合物进行 -选择性取代。
Beilstein J Org Chem. 2018 May 14;14:1039-1045. doi: 10.3762/bjoc.14.91. eCollection 2018.
7
Hypervalent iodine mediated synthesis of carbamate protected p-quinone monoimine ketals and p-benzoquinone monoketals.高价碘介导的氨基甲酸酯保护的对苯醌单亚胺缩酮和对苯醌单酮的合成。
Org Biomol Chem. 2012 Jun 21;10(23):4549-53. doi: 10.1039/c2ob25089f. Epub 2012 May 8.
8
How the combination of PhIO and I provides a species responsible for conducting organic reactions through radical mechanisms.PhIO和I的组合如何产生一种通过自由基机制进行有机反应的物质。
Org Biomol Chem. 2020 Oct 21;18(40):8103-8108. doi: 10.1039/d0ob01705a.
9
Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins.碘苯并恶唑介导的烯烃三组分硒官能化反应。
J Org Chem. 2021 Apr 2;86(7):5292-5304. doi: 10.1021/acs.joc.1c00257. Epub 2021 Mar 11.
10
I(2)-mediated carbamate annulation: scope and application in the synthesis of azasugars.I(2)-介导的氨基甲酸酯环化反应：在azasugars 合成中的范围和应用。
Carbohydr Res. 2012 Jul 15;356:163-71. doi: 10.1016/j.carres.2012.03.015. Epub 2012 Mar 23.
本文引用的文献
1
Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/-acyliminium ion cyclization cascade.通过Ugi/酰亚胺离子环化串联反应构建功能化的三环二氢吡嗪并喹唑啉二酮化学结构类型
Tetrahedron Lett. 2013 Aug 14;54(33):4467-4470. doi: 10.1016/j.tetlet.2013.06.042.
2
Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis.作为潜在且有选择性的结核分枝杆菌抑制剂的 mycobactin 类似物的合成。
Org Biomol Chem. 2012 Oct 7;10(37):7584-93. doi: 10.1039/c2ob26077h. Epub 2012 Aug 16.
3
Concise asymmetric total synthesis of 9-epi-sessilifoliamide J.9-表塞西利福酰胺 J 的简洁非对映全合成
Org Lett. 2011 Oct 7;13(19):5270-3. doi: 10.1021/ol202140y. Epub 2011 Aug 31.
4
2-Propyl 3,3-dibromo-2-hydroxy-pyrrolidine-1-carboxyl-ate.2-丙基-3,3-二溴-2-羟基吡咯烷-1-羧酸酯
Acta Crystallogr Sect E Struct Rep Online. 2010 Feb 13;66(Pt 3):o597. doi: 10.1107/S1600536810005106.
5
Chemistry of polyvalent iodine.多价碘的化学性质
Chem Rev. 2008 Dec;108(12):5299-358. doi: 10.1021/cr800332c.
6
Catalytic asymmetric total synthesis of (+)-yohimbine.（+）-育亨宾的催化不对称全合成。
Org Lett. 2008 Mar 6;10(5):745-8. doi: 10.1021/ol702781q. Epub 2008 Feb 8.
7
Cyclizations of N-acyliminium ions.N-酰基亚胺离子的环化反应。
Chem Rev. 2004 Mar;104(3):1431-628. doi: 10.1021/cr0306182.
8
Polyvalent iodine in organic chemistry.有机化学中的多价碘
J Org Chem. 2003 Apr 18;68(8):2997-3008. doi: 10.1021/jo030022e.
9
Organic Polyvalent Iodine Compounds.有机多价碘化合物
Chem Rev. 1996 May 9;96(3):1123-1178. doi: 10.1021/cr940424+.
10
Addition of a Chiral Boron Enolate to Cyclic N-Acyliminium Ions. Stereocontrolled Synthesis of the Pyrrolizidine Ring System.手性硼烯醇盐与环状N-酰基亚胺离子的加成反应。吡咯里西啶环系的立体控制合成。
J Org Chem. 1996 May 3;61(9):3187-3190. doi: 10.1021/jo9513020.
Zotero 插件