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Front Cover: Novel Ambergris Odorants Devoid of Ketal Functions: Sustainable Synthesis of 4-(α-Cedren-8-yl)Butan-2-Ones and Potent Methoxy Derivatives by Claisen Chemistry (Eur. J. Org. Chem. 33/2025) 封面：新型无酮功能龙香气味剂：clisen化学可持续合成4-（α-雪松-8-基）丁酮-2- 1和有效的甲氧基衍生物。j . Org。化学33/2025)
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.70084
Elisa Kuhnt, Marc Mansfeld, Philip Kraft
{"title":"Front Cover: Novel Ambergris Odorants Devoid of Ketal Functions: Sustainable Synthesis of 4-(α-Cedren-8-yl)Butan-2-Ones and Potent Methoxy Derivatives by Claisen Chemistry (Eur. J. Org. Chem. 33/2025)","authors":"Elisa Kuhnt,&nbsp;Marc Mansfeld,&nbsp;Philip Kraft","doi":"10.1002/ejoc.70084","DOIUrl":"10.1002/ejoc.70084","url":null,"abstract":"<p><b>The Front Cover</b> features a highly potent methoxy-substituted constituent of the novel ambergris odorant “Ambronova”, docked to the olfactory receptor OR7A17, assumed to be responsible for eliciting ambergris odor sensations. To remain in the cosmic context, the receptor surface was rendered as an emission nebula of a supernova remnant, and its excellent fit with the molecular features demonstrates the high degree of complementarity with the bifunctional methoxy ketone that mimics a ketal function. More information can be found in the Research Article by P. Kraft and co-workers (DOI: 10.1002/ejoc.202500548).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 33","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.70084","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145117213","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Site‐Selective CH Amination of Lupane‐Type Triterpenoids Lupane型三萜的位点选择性C - H胺化
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500340
Vladislavs Kroškins , Jevgeņija Lugiņina , Rihards Lācis , Anatoly Mishnev , Māris Turks
{"title":"Site‐Selective CH Amination of Lupane‐Type Triterpenoids","authors":"Vladislavs Kroškins ,&nbsp;Jevgeņija Lugiņina ,&nbsp;Rihards Lācis ,&nbsp;Anatoly Mishnev ,&nbsp;Māris Turks","doi":"10.1002/ejoc.202500340","DOIUrl":"10.1002/ejoc.202500340","url":null,"abstract":"<div><div>A synthetic protocol for rhodium‐catalyzed, site‐selective CH amination of the betulin scaffold has been developed. Under catalytic conditions, betulin‐derived 28‐<em>O</em>‐sulfamate ester undergoes intramolecular CH amination to afford 1,2,3‐oxathiazinane‐2,2‐dione‐fused lupane triterpenoids with a C16/C22 selectivity ratio 9:1. Introduction of a C16‐substituent enables a second sequential CH amination, which occurs with C22 selectivity. Betulin‐derived oxathiazinanes can be cleaved and the ring‐opened products provide straightforward access to 16‐amino‐ and 16‐azido‐betulin, 16‐amino‐betulinic, and 16‐amino‐betulonic acids. Betulin analogs with selectively introduced amine and azide functionalities are versatile building blocks for further medicinal chemistry applications in semisynthetic triterpenoid series.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500340"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144201550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Facile Synthesis of 5‐Halo‐1,2,3‐Triazole‐Fused Benzotricyclic Frameworks from 1‐(ω‐Azidoalkyl)‐2‐(2,2‐Dihalovinyl)Arenes and their Application in Fluorescent Triazole Derivatives 1-（ω-叠氮烷基）-2-（2,2-二卤乙烯基）芳烃催化合成5- halo -1,2,3-三唑-并杂三环骨架及其在荧光三唑衍生物中的应用
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500355
Seiya Kikukawa , Miki Ebihara , Kazuki Kobayashi , Nozomi Kasakura , Takashi Kanamori , Tadaomi Furuta , Ai Kohata , Nobuaki Funahashi , Shota Matsumoto , Satoru Karasawa , Kazushi Kinbara , Naohiko Koshikawa , Hideya Yuasa , Takeshi Hata
{"title":"Facile Synthesis of 5‐Halo‐1,2,3‐Triazole‐Fused Benzotricyclic Frameworks from 1‐(ω‐Azidoalkyl)‐2‐(2,2‐Dihalovinyl)Arenes and their Application in Fluorescent Triazole Derivatives","authors":"Seiya Kikukawa ,&nbsp;Miki Ebihara ,&nbsp;Kazuki Kobayashi ,&nbsp;Nozomi Kasakura ,&nbsp;Takashi Kanamori ,&nbsp;Tadaomi Furuta ,&nbsp;Ai Kohata ,&nbsp;Nobuaki Funahashi ,&nbsp;Shota Matsumoto ,&nbsp;Satoru Karasawa ,&nbsp;Kazushi Kinbara ,&nbsp;Naohiko Koshikawa ,&nbsp;Hideya Yuasa ,&nbsp;Takeshi Hata","doi":"10.1002/ejoc.202500355","DOIUrl":"10.1002/ejoc.202500355","url":null,"abstract":"<div><div>By heating 1‐(ω‐azidoalkyl)‐2‐(2,2‐dihalovinyl)arenes in DMF, intramolecular Huisgen cycloaddition between the azido group and the 1,1‐dihalovinyl moiety proceeds smoothly to afford 5‐halo‐1,2,3‐triazole‐fused tricyclic benzocondensed compounds. Leveraging the remaining halogen groups, the carbon chain extension via the Mizoroki–Heck or Suzuki–Miyaura coupling reactions, followed by an intramolecular Friedel–Crafts reaction, furnish polycyclic systems that incorporate fused triazole rings. Furthermore, the transformation of the halogen groups into the 2‐nitrobenzene derivatives via Suzuki–Miyaura cross‐coupling, followed by a Cadogan reaction using triphenylphosphine, provides a series of fluorescent pentacyclic compounds.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500355"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Kinetic Resolution of Secondary Alcohols Using Connon Type Catalysts 用Connon型催化剂动力学拆分仲醇
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500733
Caroline M. Carter , Hendrik Zipse
{"title":"Kinetic Resolution of Secondary Alcohols Using Connon Type Catalysts","authors":"Caroline M. Carter ,&nbsp;Hendrik Zipse","doi":"10.1002/ejoc.202500733","DOIUrl":"10.1002/ejoc.202500733","url":null,"abstract":"<div><div>Chiral pyridine derivatives following the general design principle proposed by Connon et al. are employed in the Lewis base mediated kinetic resolution of secondary alcohols. Variations in the size of substrates and catalyst substituents are found to impact reaction selectivity in a nonsystematic manner, while best selectivities are found for catalyst variants carrying electron‐acceptor‐substituted side chains. Solvent effects are found to be small for the most active and most selective catalysts studied, but more significant for less selective catalysts. The quantitative assessment of reaction kinetics points to a rather limited contribution of background acylation reactivity, but to a very significant temperature effect on reaction outcome.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500733"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144747600","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Fluorescent β‐Sheet‐Based Peptide Hydrogels with Aggregation‐Enhanced Emission Properties 具有聚集增强发射特性的基于β -薄片的荧光肽水凝胶
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500730
Jolien Bertouille , Adelaide R. Mashweu , François J. De Beer , Charlotte Yvanoff , Ronnie G. Willaert , Steven Ballet , Charlotte Martin , Vladimir A. Azov , Ulrich Hennecke
{"title":"Fluorescent β‐Sheet‐Based Peptide Hydrogels with Aggregation‐Enhanced Emission Properties","authors":"Jolien Bertouille ,&nbsp;Adelaide R. Mashweu ,&nbsp;François J. De Beer ,&nbsp;Charlotte Yvanoff ,&nbsp;Ronnie G. Willaert ,&nbsp;Steven Ballet ,&nbsp;Charlotte Martin ,&nbsp;Vladimir A. Azov ,&nbsp;Ulrich Hennecke","doi":"10.1002/ejoc.202500730","DOIUrl":"10.1002/ejoc.202500730","url":null,"abstract":"<div><div>Novel fluorescent peptide hydrogels are reported by combining 1,8‐naphthalimide‐derived amino acids with a previously developed peptide‐based controlled drug release matrix. Aggregation‐enhanced emission is achieved by inserting the fluorescent naphthalimide moieties in a peptide sequence with self‐assembling properties. The formation of β‐sheets directs the orientation of the luminescent side chains, leading to the avoidance of aggregation‐caused quenching. The relation between the β‐sheet‐underpinned fiber formation and the emission characteristics is further elucidated by spectroscopic and microscopic techniques, including correlative fluorescence and atomic force microscopy imaging. Owing to the incorporation of the naphthalimide moiety, the gelation concentration is lowered and the gel strength improved. The resulting hydrogels does not contain any organic solvent (in contrast to ample literature examples), present thixotropic behavior, and the fluorescent properties are sensitive to environmental conditions such as temperature and medium. These features make the soft biomaterials interesting for applications such as biosensing, real‐time bioimaging, and 3D printing. The high tunability of the peptide sequence composition and configuration, as well as the chemical structure of the 1,8‐naphthalimide moiety, allows for modulating the material toward desired properties.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500730"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144763496","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nucleophilic Substitution of Alkyl Halides with Secondary Phosphine Oxides under Solvent‐Free Conditions for the Synthesis of Tertiary Phosphine Oxides 在无溶剂条件下，烷基卤化物与仲膦氧化物的亲核取代合成叔膦氧化物
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500229
Yuying Chen , Xiaoyu Yan , Jing Yu , Yingying Su , Zheng Liu , Mengcheng Zhang , Xiantao Ma
{"title":"Nucleophilic Substitution of Alkyl Halides with Secondary Phosphine Oxides under Solvent‐Free Conditions for the Synthesis of Tertiary Phosphine Oxides","authors":"Yuying Chen ,&nbsp;Xiaoyu Yan ,&nbsp;Jing Yu ,&nbsp;Yingying Su ,&nbsp;Zheng Liu ,&nbsp;Mengcheng Zhang ,&nbsp;Xiantao Ma","doi":"10.1002/ejoc.202500229","DOIUrl":"10.1002/ejoc.202500229","url":null,"abstract":"<div><div>The development of a metal‐free Michaelis–Arbuzov reaction for green and efficient construction of CP(V) compounds represents a significant advancement in organophosphorus synthesis. Herein, a nucleophilic substitution strategy between alkyl halides and secondary phosphine oxides under solvent‐ and metal‐free conditions is reported, using sodium iodide as the catalytic promoter. This method provides a facile operation for the synthesis of diverse tertiary phosphine oxides with significant advantages. Firstly, the reaction exhibits broad substrate compatibility, covering a range of aliphatic halides and phosphorus nucleophiles. Secondly, it can be scaled up to the gram level without sacrificing efficiency, and the reaction pathway clearly established through rational studies. Particularly noteworthy is the complete elimination of transition metal catalysts and organic solvents, which aligns with the principles of green chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500229"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144715655","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Concave Mirror Photoreactor Design for Visible‐Light Photocatalysis 一种用于可见光光催化的凹面镜光反应器设计
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500568
Marko Slijepcevic , Milica Plazinic , Filip Bihelovic , Bojan Vulovic
{"title":"A Concave Mirror Photoreactor Design for Visible‐Light Photocatalysis","authors":"Marko Slijepcevic ,&nbsp;Milica Plazinic ,&nbsp;Filip Bihelovic ,&nbsp;Bojan Vulovic","doi":"10.1002/ejoc.202500568","DOIUrl":"10.1002/ejoc.202500568","url":null,"abstract":"<div><div>A novel photoreactor design for enhanced reaction efficiency and reproducibility is disclosed. The performance of the new setup with a spherical mirror‐like architecture is evaluated through six versatile visible‐light‐driven transformations reported in the literature. Inexpensive, modular, and adaptable, photoreactor enables an increase in optical power and provides significant acceleration of photocatalytic reactions in all cases. Parallel experiments as well as small‐scale chemistry are also examined.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500568"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145128906","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Transition Metal‐Free Carboxylation of Aryl Boronates in Supercritical CO2 过渡-无金属硼酸芳基在超临界CO2中的羧基化
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500290
Jun Odake , Naoyuki Toriumi , Masanobu Uchiyama
{"title":"Transition Metal‐Free Carboxylation of Aryl Boronates in Supercritical CO2","authors":"Jun Odake ,&nbsp;Naoyuki Toriumi ,&nbsp;Masanobu Uchiyama","doi":"10.1002/ejoc.202500290","DOIUrl":"10.1002/ejoc.202500290","url":null,"abstract":"<div><div>Carboxylation using stable and abundant CO<sub>2</sub> as a carbon source is an attractive option in synthetic organic chemistry if the use of highly reactive organometals or toxic and expensive transition metals can be avoided. Herein a transition metal‐free direct carboxylation of aryl trialkoxyboronates in supercritical CO<sub>2</sub> (scCO<sub>2</sub>), promoted by a catalytic amount of ZnO, is reported. The use of cage‐shaped trialkoxyboronates, which are both nucleophilic and soluble in scCO<sub>2</sub>, is the key to this reaction. density functional theory calculations indicate that the high pressure and high temperature of scCO<sub>2</sub> with the ZnO catalyst compensate for the high activation energy of direct carboxylation of the boronates.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500290"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144104023","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Exploring the Chemical Reactivity of Triisopropylsilyl Dialkynylmethanol for the Synthesis of Dialkynylcarbinol‐Related Compounds 探索三异丙基硅基二炔基甲醇合成二炔基甲醇相关化合物的化学反应性
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500762
Maria Vieira de Brito, François‐Xavier Toublet, Margaux Bossuat, Dalila Maria Barbosa Davi, Diana Kelly Almeida, Thiago de Sousa Fonseca, Fátima Miranda Nunes, Marcos Carlos de Mattos, Maëlle Caroff, Sébastien Britton, Stéphanie Ballereau, Valérie Maraval, Maria Conceição Ferreira Oliveira, Yves Génisson, Vania Bernardes‐Génisson
{"title":"Exploring the Chemical Reactivity of Triisopropylsilyl Dialkynylmethanol for the Synthesis of Dialkynylcarbinol‐Related Compounds","authors":"Maria Vieira de Brito, François‐Xavier Toublet, Margaux Bossuat, Dalila Maria Barbosa Davi, Diana Kelly Almeida, Thiago de Sousa Fonseca, Fátima Miranda Nunes, Marcos Carlos de Mattos, Maëlle Caroff, Sébastien Britton, Stéphanie Ballereau, Valérie Maraval, Maria Conceição Ferreira Oliveira, Yves Génisson, Vania Bernardes‐Génisson","doi":"10.1002/ejoc.202500762","DOIUrl":"https://doi.org/10.1002/ejoc.202500762","url":null,"abstract":"Prompted by the pharmacological relevance of lipidic alkynylcarbinols, 1‐(triisopropylsilyl)penta‐1,4‐diyn‐3‐ol is exploited as a versatile C5 organic framework. Selective functionalization of this dissymmetrical dialkynylcarbinol precursor is achieved via the creation of either a Csp–Csp (alkyne), a Csp–Csp<jats:sup>2</jats:sup> (alkene and aryl), or a Csp–Csp<jats:sup>3</jats:sup> (RCHOH) bond. A novel series of racemic HSD17B11‐bioactivated procytotoxic acetylenic lipids is accessed that revealed, amongst the most potent to date, with IC<jats:sub>50</jats:sub> down to 27 nM on osteosarcoma U2OS cells. Click‐type 1,3‐dipolar cycloadditions, such as a copper‐catalyzed reaction with a long‐chain alkyl azide (CuAAC) and a base‐promoted reaction with a lipidic nitrile oxide, are first described in a racemic version. Preparation of both enantiomers of 1‐(triisopropylsilyl)penta‐1,4‐diyn‐3‐ol through kinetic enzymatic resolution with CAL‐B immobilized on acrylic resin is carefully optimized. Finally, the use of resolved samples in 1,3‐dipolar cycloaddition reactions leads to the enantioenriched cycloadducts without significant epimerization of the carbinol center.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145116673","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Hypervalent Iodine Reagent‐Promoted Alkoxylation of Indole Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles 高价碘试剂促进吲哚衍生物烷氧基化：3,3 -二取代吲哚的合成
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI: 10.1002/ejoc.202500636
Shan‐Shan Zhang , Muzi Li , Qing Gu , Shu‐Li You
{"title":"Hypervalent Iodine Reagent‐Promoted Alkoxylation of Indole Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles","authors":"Shan‐Shan Zhang ,&nbsp;Muzi Li ,&nbsp;Qing Gu ,&nbsp;Shu‐Li You","doi":"10.1002/ejoc.202500636","DOIUrl":"10.1002/ejoc.202500636","url":null,"abstract":"<div><div>A catalyst‐free intermolecular dearomatization reaction of indoles with hypervalent‐iodine‐based nitrooxylating reagent is reported. Various alkoxyated 3,3‐disubstituted oxindoles bearing a quaternary carbon stereogenic center are obtained in good to excellent yields (up to 92%) under mild conditions. Meanwhile, the obtained products can undergo a variety of transformations smoothly, including Sonogashira coupling reaction, Suzuki coupling reaction, and demethylation reaction mediated by BBr<sub>3</sub>. In addition, natural product (±)‐convolutamydine A is synthesized by employing this method as the key step, showcasing the synthetic potential of the current method.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 34","pages":"Article e202500636"},"PeriodicalIF":2.7,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144792807","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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