钯催化的 N-叔戊基吲哚合成。
Palladium-catalyzed synthesis of N-tert-prenylindoles.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
Org Lett. 2013 Jun 7;15(11):2798-801. doi: 10.1021/ol4011344. Epub 2013 May 28.
Abstract
Palladium-catalyzed N-tert-prenylations of indoles, tricarbonylchromium-activated indoles, and indolines that occur in high yields (up to 94%) with high tert-prenyl-to-n-prenyl selectivity (up to 12:1) are reported.
摘要
报道了钯催化的吲哚、三羰基铬激活的吲哚和吲哚啉的 N-叔戊基化反应，这些反应具有高产率（高达 94%）和高的叔戊基-正戊基选择性（高达 12:1）。
相似文献
1
Palladium-catalyzed synthesis of N-tert-prenylindoles.钯催化的 N-叔戊基吲哚合成。
Org Lett. 2013 Jun 7;15(11):2798-801. doi: 10.1021/ol4011344. Epub 2013 May 28.
2
Enantioselective Arylative Dearomatization of Indoles via Pd-Catalyzed Intramolecular Reductive Heck Reactions.通过 Pd 催化的分子内还原 Heck 反应实现吲哚的对映选择性芳基化去芳构化。
J Am Chem Soc. 2015 Apr 22;137(15):4936-9. doi: 10.1021/jacs.5b01705. Epub 2015 Apr 10.
3
Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.钯催化合成N-乙烯基吡咯和吲哚。
J Org Chem. 2005 Oct 14;70(21):8638-41. doi: 10.1021/jo051450i.
4
Pd-Catalyzed asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)indoles.钯催化的 3-(对甲苯磺酰胺基烷基)吲哚的不对称氢化反应。
Org Biomol Chem. 2012 Feb 14;10(6):1235-8. doi: 10.1039/c1ob06777j. Epub 2011 Dec 19.
5
Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines.钯催化 3-(邻三氟乙酰氨基芳基)-1-丙炔醇和胺合成 2-(氨甲基)吲哚。
J Org Chem. 2014 Jan 3;79(1):401-7. doi: 10.1021/jo401456x. Epub 2013 Dec 18.
6
Decarboxylative acylation of indolines with α-keto acids under palladium catalysis: a facile strategy for the synthesis of 7-substituted indoles.钯催化下吲哚啉与α-酮酸的脱羧酰化反应：一种合成7-取代吲哚的简便策略。
Chem Commun (Camb). 2014 Nov 25;50(91):14249-52. doi: 10.1039/c4cc06929c.
7
Palladium(0)-catalyzed dearomative arylation of indoles: convenient access to spiroindolenine derivatives.钯(0)催化吲哚的去芳构化芳基化反应：方便地获得螺吲哚啉衍生物。
Org Lett. 2012 Jul 20;14(14):3772-5. doi: 10.1021/ol301663h. Epub 2012 Jul 12.
8
Palladium-catalyzed direct C-2 arylation of indoles with potassium aryltrifluoroborate salts.钯催化吲哚与芳基三氟硼酸钾盐的直接C-2芳基化反应。
J Org Chem. 2008 Sep 19;73(18):7428-31. doi: 10.1021/jo801371w. Epub 2008 Aug 15.
9
Palladium-catalyzed direct C2 arylation of N-substituted indoles with 1-aryltriazenes.钯催化的N-取代吲哚与1-芳基三氮烯的直接C2芳基化反应。
Chem Asian J. 2014 Sep;9(9):2584-9. doi: 10.1002/asia.201402274. Epub 2014 Jun 11.
10
Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.钯催化的2,3-二取代吲哚的β-烯丙基化反应
Org Lett. 2008 Jun 19;10(12):2381-4. doi: 10.1021/ol8006277. Epub 2008 May 21.
引用本文的文献
1
Recent Developments on the Synthesis and Bioactivity of Ilamycins/Rufomycins and Cyclomarins, Marine Cyclopeptides That Demonstrate Anti-Malaria and Anti-Tuberculosis Activity.近期关于伊拉霉素/红霉胺和环马菌素，以及具有抗疟疾和抗结核活性的海洋环肽的合成和生物活性的研究进展。
Mar Drugs. 2021 Aug 3;19(8):446. doi: 10.3390/md19080446.
2
Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.炔烃氢杂芳基化反应：通过 Rh-氢化物催化实现吲哚和炔烃的对映选择性偶联。
J Am Chem Soc. 2017 Aug 9;139(31):10641-10644. doi: 10.1021/jacs.7b05893. Epub 2017 Jul 25.
3
Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.通过去芳构化共轭烯丙基环化快速合成多异戊烯基化酰基间苯三酚类似物。
J Am Chem Soc. 2014 Aug 20;136(33):11799-804. doi: 10.1021/ja5060302. Epub 2014 Aug 7.
本文引用的文献
1
Enantioselective synthesis of (+)-malbrancheamide B.对映选择性合成 (+)-马布兰奇酰胺 B。
J Org Chem. 2013 Mar 15;78(6):2422-9. doi: 10.1021/jo3026059. Epub 2013 Feb 8.
2
Complexity generation in fungal peptidyl alkaloid biosynthesis: a two-enzyme pathway to the hexacyclic MDR export pump inhibitor ardeemin.真菌肽生物碱生物合成中的复杂性生成：六环 MDR 外排泵抑制剂阿黛菌素的双酶途径。
ACS Chem Biol. 2013 Apr 19;8(4):741-8. doi: 10.1021/cb3006787. Epub 2013 Feb 6.
3
Multisite prenylation of 4-substituted tryptophans by dimethylallyltryptophan synthase.二甲烯丙基色氨酸合酶对 4-取代色氨酸的多位点 prenylation。
J Am Chem Soc. 2013 Feb 6;135(5):1895-902. doi: 10.1021/ja310734n. Epub 2013 Jan 28.
4
Asymmetric cross-coupling of aryl triflates to the benzylic position of benzylamines.芳基三氟甲磺酸酯与苄胺苄基位置的不对称交叉偶联反应。
Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11510-3. doi: 10.1002/anie.201201874. Epub 2012 Oct 4.
5
Identification of a brevianamide F reverse prenyltransferase BrePT from Aspergillus versicolor with a broad substrate specificity towards tryptophan-containing cyclic dipeptides.鉴定出具有广泛色氨酸含环二肽底物特异性的粗糙脉孢菌 BrePT 短尾霉素 F 反向 prenyltransferase。
Appl Microbiol Biotechnol. 2013 Feb;97(4):1649-60. doi: 10.1007/s00253-012-4130-0. Epub 2012 Jun 3.
6
Prenylation of a nonaromatic carbon of indolylbutenone by a fungal indole prenyltransferase.真菌吲哚异戊烯基转移酶对吲哚丁烯酮的非芳碳的异戊烯基化。
Org Lett. 2012 Jun 15;14(12):3080-3. doi: 10.1021/ol301129x. Epub 2012 May 30.
7
Asymmetric N-allylation of indoles through the iridium-catalyzed allylic alkylation/oxidation of indolines.通过铱催化的二氢吲哚烯丙基烷基化/氧化反应实现吲哚的不对称N-烯丙基化反应。
Angew Chem Int Ed Engl. 2012 May 21;51(21):5183-7. doi: 10.1002/anie.201200649. Epub 2012 Apr 11.
8
Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.NotB 在诺托酰胺吲哚生物碱生物合成中作为 FAD 依赖性氧化酶的生化特征。
J Am Chem Soc. 2012 Jan 18;134(2):788-91. doi: 10.1021/ja2093212. Epub 2011 Dec 28.
9
Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.钯催化的（η6-芳基-CH2Z）Cr(CO)3 基亲核试剂的烯丙基取代反应。
J Am Chem Soc. 2011 Dec 21;133(50):20552-60. doi: 10.1021/ja208935u. Epub 2011 Nov 29.
10
Synthesis of α,α-disubstituted aryl amines by rhodium-catalyzed amination of tertiary allylic trichloroacetimidates.铑催化的叔烯丙基三氯乙酰胺的氨化反应合成α,α-二取代芳基胺。
Org Lett. 2011 Oct 21;13(20):5576-9. doi: 10.1021/ol202313y. Epub 2011 Sep 29.
Zotero 插件