European Journal of Organic Chemistry最新文献_第2页

Access to 1, 2‐Dihydropyridine/Pyridine‐Fused Coumarins through [3+3] Annulation between 4‐Aminocoumarins and Propargylic Alcohols 通过4 -氨基香豆素和丙炔醇之间的[3+3]环反应获得1,2 -二氢吡啶/吡啶融合香豆素

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401244

Minghui Liu , Pengcheng Guan , Yujie Qu , Feng Yan , Feng Feng , Chengyu Wang

引用次数: 0

A P‐nucleophile Interrupted Seyferth‐Gilbert Reaction 一种P -亲核试剂阻断了Seyferth - Gilbert反应

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401286

Yuan‐Jie Wei , Fei‐Long Zhou , Yan Tian , Prof. Dr. Yong‐Feng Cheng

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Guaiacylglycerol as an Intermediate in Vanillin Production during Oxidative Conversion of Guaiacyl Lignin under Alkaline Conditions 愈创木酰甘油在碱性条件下愈创木酰木质素氧化转化过程中生产香兰素的中间体。

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401272

Takuya Hayashi , Ayami Ishikawa , Takashi Hosoya , Hisashi Miyafuji

{"title":"Guaiacylglycerol as an Intermediate in Vanillin Production during Oxidative Conversion of Guaiacyl Lignin under Alkaline Conditions","authors":"Takuya Hayashi , Ayami Ishikawa , Takashi Hosoya , Hisashi Miyafuji","doi":"10.1002/ejoc.202401272","DOIUrl":"10.1002/ejoc.202401272","url":null,"abstract":"<div><div>Depolymerizing lignin into hydroxybenzaldehydes like vanillin via oxidative degradation is a promising approach for lignin valorization. Alkaline nitrobenzene (AN) oxidation is a highly selective method for oxidative lignin conversion and serves as a benchmark in lignin chemistry, yet its reaction mechanisms are not fully understood. Previously, we proposed a pathway converting a phenolic β‐O‐4 model compound, <em>erythro</em>‐guaiacylglycerol‐β‐guaiacyl ether (<strong>GG</strong>), into vanillin through enol ether intermediates, <em>E</em>/<em>Z</em>‐2‐methoxy‐4‐[2‐(2‐methoxyphenoxy)‐ethenyl]‐phenol <strong>EE</strong>. This study extends that work by exploring alternative AN oxidation pathways of <strong>GG</strong> that bypass <strong>EE</strong>. Through experiments assessing the impact of OH<sup>−</sup> concentration and studying deuterium incorporation at the α‐position of vanillin produced from both <strong>GG</strong> and isolated <strong>EE</strong> in NaOD/D₂O, we identified guaiacylglycerol (<strong>GGL</strong>) as a new intermediate in a distinct pathway. <strong>GGL</strong> forms via β‐ether cleavage of a dianion arising from dual deprotonation of <strong>GG</strong>′s phenolic and α‐OH groups, a process favored under high OH<sup>−</sup> concentrations conducive to dianion formation. Subsequent oxidation of <strong>GGL</strong> yields vanillin, with significant exchange of the α‐hydrogen with solvent molecules. This study elucidates the complex mechanisms of AN oxidation and introduces novel intermediates and pathways, enhancing strategies for efficient lignin conversion into valuable chemicals.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401272"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021120","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}

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Reactions of Unsymmetric Chiral Dialdehydes with Lysine: Regio‐ and Enantioselective Macrocyclization and Fluorescent Sensing 不对称手性二醛与赖氨酸的反应：区域和对映选择性大环化和荧光传感

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401250

Yifan Mao , Yichen Li , Stephanie Davis , Lin Pu

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Quinoid Carbene Mediated C(sp2)‐Heteroatom Bond Formation 醌类碳烯介导的C(sp2)-杂原子键形成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401282

Hongying Cheng , XiaoKun Wang , Kai Tan , Xiaoyu Ren , Zhen Guo , Chengming Wang , Cong‐Ying Zhou

{"title":"Quinoid Carbene Mediated C(sp2)‐Heteroatom Bond Formation","authors":"Hongying Cheng , XiaoKun Wang , Kai Tan , Xiaoyu Ren , Zhen Guo , Chengming Wang , Cong‐Ying Zhou","doi":"10.1002/ejoc.202401282","DOIUrl":"10.1002/ejoc.202401282","url":null,"abstract":"<div><div>C(sp<sup>2</sup>)‐heteroatom bonds play a critical role in biologically active molecules, pharmaceuticals, and functional materials. Traditional methods for synthesizing these bonds often rely on transition metal‐catalyzed cross‐coupling reactions, such as the Buchwald‐Hartwig and Ullmann reactions, which have limitations, including the requirement for elevated temperature and basic conditions. In recent years, diazo quinones have emerged as promising reagents for C(sp<sup>2</sup>)‐heteroatom bond formation due to their unique structural and reactive properties, which include high electrophilicity and a tendency toward aromatization. This review highlights recent advances in the use of quinoid carbenes, derived from diazo quinones, for the construction of C(sp<sup>2</sup>)−N, C(sp<sup>2</sup>)−O, and C(sp<sup>2</sup>)−S bonds. Key methodologies discussed include rhodium‐, iridium‐, ruthenium‐ and palladium‐catalyzed cross‐coupling reactions, heteroatom‐H bond insertion reactions, migration reactions and sigmatropic rearrangements. These methods offer mild, functional group‐tolerant alternatives to traditional approaches, showcasing their utility in the synthesis of complex bioactive molecules, medicinally relevant compounds, and materials.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401282"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142905507","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}

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Diethylaluminium Chloride‐Mediated Cycloaddition/Conjugate Reduction Sequence towards Imido‐Substituted Norbornenes 二乙基氯化铝介导的亚胺取代降冰片烯的环加成/共轭还原序列

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401270

Manuel Kirchhof , Derman Batman , Elliot Nicholas , Wolfgang Frey , Volker Derdau , Anna Zens , Sabine Laschat

引用次数: 0

Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of N‐Tosyl Homopropargyl Amides to γ‐Lactams 炔基苯基硒化物在N-Tosyl同丙基酰胺无金属环化合成γ-内酰胺中的中间体作用

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401248

Andrea Temperini , Giulia Brufani , Stefano Santoro , Luigi Vaccaro

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Use of Real‐Time In‐Situ UV‐vis Spectrophotometry as a Tool for Monitoring Electrochemically‐Mediated Organic Synthesis 利用实时原位紫外可见分光光度法监测电化学介导的有机合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401266

Chelsea M. Schroeder , Nicholas E. Leadbeater

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Synthesis of Enantioenriched 2‐((Hetera)Cyclo) Alkylchromanols and their Spirocyclic Analogs through Enzymatic Resolution 酶法合成富集对映体的2-（杂环）烷基氯烷醇及其螺环类似物

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401247

Oleksii S. Timokhin , Anastasiia M. Romanova , Viktoria S. Moskvina , Olexandr V. Kucher , Aleksandr I. Boiko , Anna L. Banasevych , Dmytro Durylin , Volodymyr S. Brovarets , Prof. Dr. Oleksandr O. Grygorenko

{"title":"Synthesis of Enantioenriched 2‐((Hetera)Cyclo) Alkylchromanols and their Spirocyclic Analogs through Enzymatic Resolution","authors":"Oleksii S. Timokhin , Anastasiia M. Romanova , Viktoria S. Moskvina , Olexandr V. Kucher , Aleksandr I. Boiko , Anna L. Banasevych , Dmytro Durylin , Volodymyr S. Brovarets , Prof. Dr. Oleksandr O. Grygorenko","doi":"10.1002/ejoc.202401247","DOIUrl":"10.1002/ejoc.202401247","url":null,"abstract":"<div><div>An efficient approach to the multigram synthesis of 2‐((hetera) cyclo) alkylchromanols and their spirocyclic analogs based on enzymatic resolution is described. It is shown that enzymatic acylation could be used for the preparation of enantioenriched title compounds with primary alkyl substituents at the C‐2 position. Meanwhile, enzymatic hydrolysis of the corresponding acetates was optimal for the preparation of the target alcohols when significant steric hindrance is present, e. g., due to the α‐branching. The latter factor was demonstrated to be crucial for the enzymatic reaction rate in both cases. The synthetic utility of the obtained chiral alcohols was demonstrated through Mitsunobu configuration inversion, as well as by preparation of the corresponding primary amines – valuable <em>sp</em><sup>3</sup>‐enriched building blocks for medicinal chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401247"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929703","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

Stereoselective Strategies for the Synthesis of Functionalized cis-Hydrindanes in Natural Product Synthesis

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-02-23 DOI: 10.1002/ejoc.202500006

Vijayanand U. Survase, Kishor Laxman Handore

{"title":"Stereoselective Strategies for the Synthesis of Functionalized cis-Hydrindanes in Natural Product Synthesis","authors":"Vijayanand U. Survase, Kishor Laxman Handore","doi":"10.1002/ejoc.202500006","DOIUrl":"https://doi.org/10.1002/ejoc.202500006","url":null,"abstract":"The cis-hydrindane motif is a bicyclic structure commonly found in many natural products that exhibit significant biological activity. This structural feature is present in a variety of bioactive compounds, particularly terpenoids, steroids, and alkaloids, which are known for their therapeutic potential, including anti-inflammatory, antimicrobial, antiviral, and anticancer properties. Due to its prevalence and biological relevance, the cis-hydrindane framework has attracted considerable attention from synthetic chemists, who have devoted substantial effort toward developing efficient and diverse methods for constructing this important motif. Many of the synthesized cis-hydrindane compounds have been used as key intermediates or building blocks in the total synthesis of complex natural products. This review provides an overview of strategic approaches for synthesizing functionalized cis-hydrindanes and its derivatives from 2000 to the present day, focusing on their application in natural product synthesis. By examining the diverse methods and their impact on natural product synthesis, this review will underscore the enduring importance of the cis-hydrindane framework in both synthetic organic chemistry and medicinal chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477917","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