European Journal of Organic Chemistry最新文献_第10页

Three-Component Cycloadditions to prepare Isooxazoline-Fused Furo[3,2-b]quinolines

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-04 DOI: 10.1002/ejoc.202500007

Chun-Yu Nong, Xiu-Qing Mo, Jin-He Zhao, Lu Lei, Lu Ma, Dong-Liang Mo

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Concise Four‐Component Synthesis of Solid‐State Fluorescent α‐Sulfenylated Enaminones 固态荧光α-磺化胺酮的简洁四组分合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401308

Gereon Hendrik Schmitz , Wiebke Kramer , Leonard Karl , Christian Ganter , Thomas J. J. Müller

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Recent Development of DNA‐based Biohybrid Systems Driven by Light 基于dna的光驱动生物混合系统的最新进展

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401297

Zachary Pastorel , Juliette Zanzi , Dr. Yves Canac , Dr. Olivier Baslé , Prof. Michael Smietana

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Amino Acid‐Mediated Enantioselective Synthesis of a Bicyclic Ketocarbaldehyde: Theoretical and Experimental Insights into a Key Intermediate for Some Polycyclic Diterpene Synthesis

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401291

Francesca Leonelli , Fabrizio Vetica , Enrico Bodo , Stefano Russo , Lorenzo Michelini , Elisa Sturabotti , Giulia Mazzoccanti , Alessia Ciogli , Nicola Demitri , Doriano Lamba , Annalisa Masi , Luisa Maria Migneco , Rinaldo Marini Bettolo

{"title":"Amino Acid‐Mediated Enantioselective Synthesis of a Bicyclic Ketocarbaldehyde: Theoretical and Experimental Insights into a Key Intermediate for Some Polycyclic Diterpene Synthesis","authors":"Francesca Leonelli , Fabrizio Vetica , Enrico Bodo , Stefano Russo , Lorenzo Michelini , Elisa Sturabotti , Giulia Mazzoccanti , Alessia Ciogli , Nicola Demitri , Doriano Lamba , Annalisa Masi , Luisa Maria Migneco , Rinaldo Marini Bettolo","doi":"10.1002/ejoc.202401291","DOIUrl":"10.1002/ejoc.202401291","url":null,"abstract":"<div><div>A study on the amino acid‐mediated intramolecular cyclization of diketoaldehyde <strong>2</strong> to form bicyclic ketocarbaldehyde <strong>1</strong>, a potentially useful intermediate in the synthesis of some polycyclic diterpenes, is hereafter presented. This cyclization exhibits a peculiar enantio‐selectivity if compared to similar intramolecular cyclizations due to its product being the (<em>S</em>)‐enantiomer when using <span>d</span>‐amino acids. Our findings reveal that the transformation proceeds through two irreversible steps: the cyclization and the subsequent dehydration process. The reaction enantiomeric excess (e.e.) was optimized by systematically varying the amino acids, solvents, and acids used. Aldol intermediates were successfully isolated. The structure of the most abundant one was confirmed by X‐ray analysis, which supported the proposed reaction mechanism. NMR and MS were employed to monitor in real‐time the formation and the evolution of these intermediates. This approach allowed us to detect the key species that contribute to the enantioselectivity and yield of the final product. Additionally, the transition state energies associated with the formation of the eight possible aldol intermediates were examined through computational studies, further elucidating the mechanistic pathway of this enantioselective cyclization.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 9","pages":"Article e202401291"},"PeriodicalIF":2.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401291","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143124959","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}

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A Quinidine‐Based Squaramide‐Catalyzed Asymmetric Cascade Double Hetero‐Michael Addition‐Cyclization of N‐Benzylhydroxylamine: Synthesis of Chiral 1,2‐Benzoxazines 奎尼丁基角酰胺催化n-苄基羟胺的不对称级联双杂michael加成环化：手性1,2-苯并恶嗪的合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401306

Chandan Kamilya , Dipankar Das , Nikhil L. Gorane , Prof. Prasanta Ghorai

{"title":"A Quinidine‐Based Squaramide‐Catalyzed Asymmetric Cascade Double Hetero‐Michael Addition‐Cyclization of N‐Benzylhydroxylamine: Synthesis of Chiral 1,2‐Benzoxazines","authors":"Chandan Kamilya , Dipankar Das , Nikhil L. Gorane , Prof. Prasanta Ghorai","doi":"10.1002/ejoc.202401306","DOIUrl":"10.1002/ejoc.202401306","url":null,"abstract":"<div><div>The double hetero‐Michael addition (DHMA), leveraging the reactivity of two distinct nucleophilic centers (oxygen and nitrogen), has emerged as a transformative strategy in organic synthesis for constructing carbon‐hetero nuclear bonds in a single step. In this work, we report an innovative intermolecular DHMA cascade cyclization reaction catalyzed by a quinidine‐based squaramide catalyst. The use of the squaramide catalyst is particularly noteworthy, as it enhances the electrophilicity of the <em>α</em>,<em>β</em>‐unsaturated <em>bis</em>‐enone, thereby promoting excellent enantioselective formation of the 1,2‐benzoxazine. The process demonstrates excellent enantiomeric excess (up to 99 % ee), moderate diastereoselectivity (up to 6 : 1 dr), and high yields. The four different 1,2‐benzoxazine stereoisomers have been synthesized with excellent enantiomeric excess. Furthermore, the scaleup reaction of the methodology has been extended with excellent outcomes.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 9","pages":"Article e202401306"},"PeriodicalIF":2.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142991636","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

Recent Advances in Zinc‐Catalyzed Carbon‐Heteroatom Bond Formation

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401271

Julio Álvarez‐Valle , Patricia García‐Martínez , Luis A. López , Javier Santamaría

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Recent Advances in the Synthesis of Nitrogen‐Containing Heterocycles Based on Hydrazine‐Directed C−H Bond Activation/Annulation Reactions

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401233

He Li , Tao Chen , Baoheng Wu , Xinxin Jin , Jinglin Liu , Ming Bao

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Cs2CO3‐I2 Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin Cs2CO3‐I2促进黄酮和黄酮的高效合成：纳兰根素和芹菜素的全合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401298

Kailas Arjun Chavan , Dr. Rohan D. Erande

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5‐Substituted 1,2‐Dihydroxyindolizidines and ‐Pyrrolizidines Related to Swainsonine: Synthesis and Inhibition Study

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401307

Peter Gabko , Dr. Sergej Šesták , Prof. Dr. Ján Moncoľ , Dr. Maroš Bella

{"title":"5‐Substituted 1,2‐Dihydroxyindolizidines and ‐Pyrrolizidines Related to Swainsonine: Synthesis and Inhibition Study","authors":"Peter Gabko , Dr. Sergej Šesták , Prof. Dr. Ján Moncoľ , Dr. Maroš Bella","doi":"10.1002/ejoc.202401307","DOIUrl":"10.1002/ejoc.202401307","url":null,"abstract":"<div><div>Development of selective Golgi α‐mannosidase II inhibitors possessing a modified swainsonine skeleton has recently become a popular field of study due to their great potential in suppressing metastasis. However, most of the studied modifications involve addition of a substituent on the bicycle which makes the synthesis rather complex as five stereogenic centres have to be generated. Inspired by our previously developed synthesis of (5<em>S</em>)‐5‐benzylswainsonines utilizing a fully stereoselective intramolecular reductive amination, we decided to further investigate the versatility of this strategy by preparing a small collection of simplified analogues bearing only two hydroxy groups, thus eliminating one of the stereogenic centres. This contribution reports a concise synthesis of 5‐substituted 1,2‐dihydroxyindolizidines and ‐pyrrolizidines whose key features include small number of steps, high yields and excellent stereoselectivity. The title compounds were also tested for inhibitory activity against a Golgi and a lysosomal α‐mannosidase to assess the effects of the substituents, ring size and missing C8‐hydroxyl on potency and selectivity.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 9","pages":"Article e202401307"},"PeriodicalIF":2.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393844","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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A Meta‐Analysis of Published Brønsted Plots Supports Brønsted's “Conventional” pKa Values: 14.00 for Water and 0.00 for H+(aq)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-03-03 DOI: 10.1002/ejoc.202401135

Todd P. Silverstein , Thomas Neils

{"title":"A Meta‐Analysis of Published Brønsted Plots Supports Brønsted's “Conventional” pKa Values: 14.00 for Water and 0.00 for H+(aq)","authors":"Todd P. Silverstein , Thomas Neils","doi":"10.1002/ejoc.202401135","DOIUrl":"10.1002/ejoc.202401135","url":null,"abstract":"<div><div>In the early 1900s, Brønsted used two different pairs of p<em>K</em><sub>a</sub> values for water and the aqueous proton: He denoted 14.00 and 0.00 (respectively) as the “conventional” values, and 15.74 and −1.74 (respectively) as the “rational” values. Although the conventional values have been supported by both experiment and theory, the rational values have been employed in the vast majority of studies involving Brønsted plots up to the present day. Here we present a meta‐analysis of 67 Brønsted plots published from 1924 to 2010, revealing that rational p<em>K</em><sub>a</sub>’ values more frequently appear as statistical outliers (a greater than 80 % rejection rate) compared to conventional values (a roughly 50 % rejection rate) based on <em>Q</em>‐tests. Furthermore, in 85 % of examined plots, the conventional points align more closely with best‐fit lines. An evaluation of Hupe and Pohl's Marcus plots also shows a somewhat better fit with the conventional rather than the rational p<em>K</em><sub>a</sub>’ values. Finally, in the bond length versus p<em>K</em><sub>a</sub> investigations published by Brydon et al., all the rational points were statistically rejected, whereas the conventional values were accepted. From our statistical analyses, we conclude that a convincing majority of experimental evidence from published Brønsted plots leads one to question the validity of Brønsted's rational p<em>K</em><sub>a</sub>’ values for water and the aqueous proton (15.74 and −1.74, respectively).</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 9","pages":"Article e202401135"},"PeriodicalIF":2.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435381","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