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DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Sulfoximines with Carboxylic Acids DMAPO/Boc2O介导的亚砜亚胺与羧酸的一锅直接N酰化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/ejoc.202500488
Atsushi Umehara, Sukenao Kawai, Makoto Sasaki
{"title":"DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Sulfoximines with Carboxylic Acids","authors":"Atsushi Umehara, Sukenao Kawai, Makoto Sasaki","doi":"10.1002/ejoc.202500488","DOIUrl":"https://doi.org/10.1002/ejoc.202500488","url":null,"abstract":"This report describes a general and simple method for the one‐pot direct N‐acylation of sulfoximines with carboxylic acids using our previously developed 4‐(N,N‐dimethylamino)pyridine N‐oxide (DMAPO)/di‐tert‐butyl dicarbonate (Boc2O) system. The method can be performed under mild low‐temperature reaction conditions and has a wide substrate scope. The present method is operationally simple, scalable, and practical, thus it should find wide applications in both academic and industrial laboratories.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488797","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
Facilitating the Isolation of Polar Natural Products: Mild 1,1’‐Carbonyldiimidazole‐Enabled Method for Derivatization of Acids and Alcohols 促进极性天然产物的分离：温和的1,1 ' -羰基二咪唑-激活方法用于酸和醇的衍生化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/ejoc.202500231
Moses M. Mutungi, Curtis C. Ho, Alex C. Bissember, Jason A. Smith
{"title":"Facilitating the Isolation of Polar Natural Products: Mild 1,1’‐Carbonyldiimidazole‐Enabled Method for Derivatization of Acids and Alcohols","authors":"Moses M. Mutungi, Curtis C. Ho, Alex C. Bissember, Jason A. Smith","doi":"10.1002/ejoc.202500231","DOIUrl":"https://doi.org/10.1002/ejoc.202500231","url":null,"abstract":"Many secondary metabolites containing carboxylic acid and alcohol functional groups are highly polar and can be difficult to purify and isolate from complex extracts obtained from natural sources. The conversion of these natural products to their corresponding alkyl esters/ carbonates under mild conditions can simplify their purification and isolation. However, traditional derivatization methods have often relied on toxic and/ or corrosive reagents that can also lead to byproduct formation or epimerization in some instances. In this work, 1,1′‐carbonyldiimidazole (CDI), a relatively inexpensive reagent with inherently low toxicity, is utilized to activate polar natural products containing carboxylic acids and alcohols to enable the formation of less polar species (N‐acylimidazoles and N‐acyloxymidazoles). These intermediates are readily converted into methyl esters and carbonates by treatment with methanol. It is anticipated that this rather simple and versatile derivatization method can facilitate the efficient isolation of secondary metabolites bearing polar carboxylic acid and alcohol residues.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488567","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
Rhodium‐Catalyzed (3+3) Cascade Cyclization of Diazobarbiturates with 2H‐Azirines for the Diastereoselective Construction of Spirooxazinopyrimidinediones 铑催化重氮巴比妥酸盐与2H -氮嘧啶的（3+3）级联环化，用于螺恶嗪嘧啶嘧啶二酮的非对映选择性构建
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ejoc.202500551
Hong-Wu Zhao, Yue Zhang, Yu-Hang Mi, Kuo Wang, Zhi-Yu Wang, Jin-Tao Li
{"title":"Rhodium‐Catalyzed (3+3) Cascade Cyclization of Diazobarbiturates with 2H‐Azirines for the Diastereoselective Construction of Spirooxazinopyrimidinediones","authors":"Hong-Wu Zhao, Yue Zhang, Yu-Hang Mi, Kuo Wang, Zhi-Yu Wang, Jin-Tao Li","doi":"10.1002/ejoc.202500551","DOIUrl":"https://doi.org/10.1002/ejoc.202500551","url":null,"abstract":"Under the catalysis of Rh2(esp)2 (10 mol%) and BINAP (20 mol%) in 1,2‐dichloroethane at 80 °C, a (3+3) cascade cyclization between diazobarbiturates and 2H‐azirines proceeded smoothly, yielding spirooxazinopyrimidinediones in 24‐92% yield with >20:1 diastereoselectivity. The chemical structure of one compound has been confirmed by X‐ray diffraction analysis, and the others are suggested by inference.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"246 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488798","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
Towards the Synthesis of 3,3‐Difluoro Deaminated Sialic Acid (C3DFKDN) 3,3‐二氟脱氨唾液酸（C3DFKDN）的合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ejoc.202500456
Lemeng Chao, Tom Wennekes
{"title":"Towards the Synthesis of 3,3‐Difluoro Deaminated Sialic Acid (C3DFKDN)","authors":"Lemeng Chao, Tom Wennekes","doi":"10.1002/ejoc.202500456","DOIUrl":"https://doi.org/10.1002/ejoc.202500456","url":null,"abstract":"2‐Keto‐3‐deoxy‐d‐glycero‐d‐galacto‐nononic acid (KDN) is a nine‐carbon monosaccharide of the sialic acid family. As a deaminated analogue of N‐acetylneuraminic acid (Neu5Ac), KDN features a hydroxyl group at C5 instead of an amine. Although present at low levels in mammalian tissues, KDN is abundant in certain tumor cells and pathogens, making it and its processing enzymes attractive targets for understanding biological functions and developing potential therapeutics. Fluorinated carbohydrate derivatives are widely used to probe and modulate carbohydrate‐active enzymes (CAZymes). Here, we report the first total synthesis of 3,3‐difluoro KDN (C3DFKDN), a novel fluorinated sialic acid derivative and a key intermediate for designing covalent inhibitors and activity‐based probes targeting KDN‐processing enzymes. Introduction of a C3‐difluoro group prevents elimination side reactions common with monofluorinated sialic acid analogues. Two synthetic strategies were explored: (1) coupling a pyranose precursor with a difluorinated alkyne bromide followed by oxidation, and (2) incorporation of a difluoroacetate building block via a Reformatsky‐type reaction. The latter approach proved more effective, affording protected C3DFKDN in an overall yield of 3.7% over 12 steps from methyl α‐d‐mannopyranoside. This work establishes methodology for the synthesis of C3‐difluorinated sialic acids and provides a foundation for developing fluorinated probes and inhibitors of KDN‐related enzymatic pathways.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"630 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488569","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
Fine-Tuning Gramicidin S: How δ-Phenylproline Affects Turns and Interaction with Membrane. 微调Gramicidin S: δ-苯脯氨酸对膜的影响及其与膜的相互作用。
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500288
Pedro Merino, Irene Sánchez-Burillo, Ana I. Jiménez, Tomás Tejero
{"title":"Fine-Tuning Gramicidin S: How δ-Phenylproline Affects Turns and Interaction with Membrane.","authors":"Pedro Merino, Irene Sánchez-Burillo, Ana I. Jiménez, Tomás Tejero","doi":"10.1002/ejoc.202500288","DOIUrl":"https://doi.org/10.1002/ejoc.202500288","url":null,"abstract":"The introduction of a phenyl ring at the 5-position of proline significantly impacts the conformation and membrane interactions of Gramicidin S. In this study, we investigate the effects of incorporating cis-5-phenyl-L-proline into Gramicidin S, focusing on its structural behavior and interaction with lipid bilayers. Using a homochiral model dipeptide, we demonstrate that cis-5-phenyl-L-proline induces a double γ-turn, altering the peptide’s folding properties. This conformational bias is then translated into Gramicidin S, where the modified structure disrupts its natural amphipathic balance, leading to unfavorable interactions with membranes. Spectroscopic and biophysical analyses confirm that the modified peptide deviates from the native β-sheet structure, likely reducing its membrane activity. These findings highlight the critical role of proline-derived structural modifications in dictating the bioactivity of cyclic peptides and provide insight into how strategic substitutions can modulate peptide-membrane interactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"34 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144370764","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
Front Cover: Terpenes and Terpenoids: How can we use them? (Eur. J. Org. Chem. 24/2025) 封面：萜烯和萜类化合物：我们如何使用它们？(欧元。j . Org。化学24/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202582401
Jay Hanssens, Diego Meneses, Jordy M. Saya, Romano V. A. Orru
{"title":"Front Cover: Terpenes and Terpenoids: How can we use them? (Eur. J. Org. Chem. 24/2025)","authors":"Jay Hanssens,&nbsp;Diego Meneses,&nbsp;Jordy M. Saya,&nbsp;Romano V. A. Orru","doi":"10.1002/ejoc.202582401","DOIUrl":"https://doi.org/10.1002/ejoc.202582401","url":null,"abstract":"<p><b>The Front Cover</b> visualizes the journey of bio-based terpenes and terpenoids, from natural feedstocks to diverse chemical platforms. It highlights their structural diversity and reactivity, showcasing their potential in green chemistry, polymer science, pharmaceuticals and synthesis. The Review by J. M. Saya, R. V. A. Orru and co-workers (DOI: 10.1002/ejoc.202401151) offers a comprehensive guide for sustainable chemical innovation by using bio-based terpene building blocks.\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 24","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202582401","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144473087","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
Synthesis of Alkylated 1-Aryl-4,5-Dimethylimidazolium-Based Tunable Aryl Alkyl Ionic Liquids (TAAILs) 烷基化1-芳基4,5-二甲基咪唑基可调芳基烷基离子液体的合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500164
Stefan Fritsch, Thomas Strassner
{"title":"Synthesis of Alkylated 1-Aryl-4,5-Dimethylimidazolium-Based Tunable Aryl Alkyl Ionic Liquids (TAAILs)","authors":"Stefan Fritsch, Thomas Strassner","doi":"10.1002/ejoc.202500164","DOIUrl":"https://doi.org/10.1002/ejoc.202500164","url":null,"abstract":"New tunable aryl alkyl ionic liquids based on 2-alkyl-1-aryl-4,5-dimethylimidazoles are synthesized using a deprotonation protocol to directly modify imidazoles without the need to rebuild the heterocyclic core. The viscosity, conductivity, and electrochemical stability of the ionic liquids are measured.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"639 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144371258","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
Front Cover: Recent Advances in Transition Metal-Free Strategies for the Transformation of Amides into Carbonyl Compounds (Eur. J. Org. Chem. 23/2025) 封面：酰胺转化为羰基化合物的过渡无金属策略的最新进展。j . Org。化学23/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202582301
Karthik Rajan Rajamanickam, Robin Prakash Sirvin Rajan, Nithin Pootheri, Chin-Fa Lee, Sunwoo Lee
{"title":"Front Cover: Recent Advances in Transition Metal-Free Strategies for the Transformation of Amides into Carbonyl Compounds (Eur. J. Org. Chem. 23/2025)","authors":"Karthik Rajan Rajamanickam,&nbsp;Robin Prakash Sirvin Rajan,&nbsp;Nithin Pootheri,&nbsp;Chin-Fa Lee,&nbsp;Sunwoo Lee","doi":"10.1002/ejoc.202582301","DOIUrl":"https://doi.org/10.1002/ejoc.202582301","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the expanding universe of transition-metal-free amide bond transformations. At the center of the image, a stylized amide framework is surrounded by orbiting motifs that represent diverse carbonyl-based derivatives and reactive intermediates. This visual composition emphasizes the wide substrate scope and synthetic utility of amides, enabling the selective formation of C─N, C─C, C─O, C─H, and C─X bonds. The dynamic layout symbolizes the conceptual shift from traditional metal-catalyzed processes to sustainable and practical alternatives in modern organic synthesis. More information can be found in the Review by C.-F. Lee, S. Lee and co-workers (DOI: 10.1002/ejoc.202500210).\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 23","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202582301","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144367419","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
Introduction of Structural Diversity at the C2 Position of Unsaturated Iminosugars through Palladium‐Catalysed Cross‐Coupling Reactions 钯催化交叉偶联反应引入不饱和亚糖C2位结构多样性
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ejoc.202500502
Yves Bleriot, angelique ferry, quentin joachim, delphine carry, mattéo di pasquale, jerome marrot, jacques uziel, nadege lubin-germain, Jerome desire, atsushi kato, suzuka yamamoto
{"title":"Introduction of Structural Diversity at the C2 Position of Unsaturated Iminosugars through Palladium‐Catalysed Cross‐Coupling Reactions","authors":"Yves Bleriot, angelique ferry, quentin joachim, delphine carry, mattéo di pasquale, jerome marrot, jacques uziel, nadege lubin-germain, Jerome desire, atsushi kato, suzuka yamamoto","doi":"10.1002/ejoc.202500502","DOIUrl":"https://doi.org/10.1002/ejoc.202500502","url":null,"abstract":"To vary the functionality of iminosugars at the C2 position, protected 2‐iodoiminoglycals in the D‐gluco, D‐galacto and D‐xylo series were efficiently synthesized from sugar lactams. Their mild palladium‐catalyzed aminocarbonylation, arylation and phosphonylation were successful and provided a range of C2‐functionalized iminoglycals in good yields. Two of these compounds were O‐deprotected to afford 1,2‐unsaturated iminosugars that proved to be modest inhibitors of glycosidases.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"640 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144370612","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 Chiron Approach to the Practical and Scalable Synthesis of the β₃-Adrenergic Receptor Agonist Vibegron β 3 -肾上腺素能受体激动剂Vibegron的实用和可扩展合成方法
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ejoc.202500469
Prakash Kumar, Santanu Karmakar, Prathama S. Mainkar, Rudrakshula Madhavachary, Srivari Chandrasekhar
{"title":"A Chiron Approach to the Practical and Scalable Synthesis of the β₃-Adrenergic Receptor Agonist Vibegron","authors":"Prakash Kumar, Santanu Karmakar, Prathama S. Mainkar, Rudrakshula Madhavachary, Srivari Chandrasekhar","doi":"10.1002/ejoc.202500469","DOIUrl":"https://doi.org/10.1002/ejoc.202500469","url":null,"abstract":"A practical and scalable synthesis of the β3-adrenergic receptor agonist Vibegron has been developed using a streamlined chiral-pool approach from readily available 4-nitro-D-phenylalanine and (R)-mandelic acid. The synthesis features a key acid-catalyzed N-acyl iminium ion cyclization followed by a highly diastereoselective reduction, enabling efficient construction of the cis-2,5-disubstituted pyrrolidine core. Final amidation with a commercially available pyrrolopyrimidine sodium salt furnished Vibegron in excellent overall yield.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144370762","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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