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Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03173
Paul Wienecke, Adriaan J. Minnaard
{"title":"Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid","authors":"Paul Wienecke, Adriaan J. Minnaard","doi":"10.1021/acs.joc.4c03173","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03173","url":null,"abstract":"Vitamin A (or all-<i>trans</i>-retinol) metabolites are involved in a wide range of cellular processes. However, the investigation of their biological role is hampered due to their very limited availability. Herein we report a stereoselective total synthesis of the vitamin A metabolites (<i>R</i>)-all-<i>trans</i>-13,14-dihydroretinol and -retinoic acid, applying an <i>E</i>-selective HWE olefination and a Ru(II) catalyzed intramolecular 7-<i>endo</i>-<i>dig</i> hydrosilylation as the key steps.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463017","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02728
Yuma Okuda, Keita Yamazaki, Tetsuhiro Nemoto
{"title":"Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates","authors":"Yuma Okuda, Keita Yamazaki, Tetsuhiro Nemoto","doi":"10.1021/acs.joc.4c02728","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02728","url":null,"abstract":"Newman–Kwart rearrangement (NKR) is a useful method for synthesizing <i>S</i>-aryl thiocarbamates from <i>O</i>-aryl thiocarbamates. Harsh temperature conditions are required, however, leading to substrate degradation and side reactions. Moreover, reactions using heteroaromatic substrates are quite rare. Herein, we report Bi(OTf)<sub>3</sub>-catalyzed NKR using heteroaromatic substrates under ambient temperature conditions. The reaction extended to not only aza-arene substrates but also thiophene substrates.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462966","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02791
Chen-Ying Zhai, Bing Zhao, Xue-Long Wang, Huai-Yan Liu, Bo Zhao, Yan Jiang
{"title":"Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones","authors":"Chen-Ying Zhai, Bing Zhao, Xue-Long Wang, Huai-Yan Liu, Bo Zhao, Yan Jiang","doi":"10.1021/acs.joc.4c02791","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02791","url":null,"abstract":"Lewis acid-enabled reactions of donor–acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the Lewis acid and the substituent at N1 of the indoline-2-thiones. With AlCl<sub>3</sub> as the Lewis acid and 1-isopropylindoline-2-thiones as reactants, a direct ring opening with DACs, followed by intramolecular nucleophilic addition/dehydration takes place leading to the formation of dihydro-2<i>H</i>-thiepino[2,3-<i>b</i>]indoles in moderate to good yields. Using Yb(OTf)<sub>3</sub> as promoter and 1-unsubstituted indoline-2-thiones as reactants, a (3 + 2) cycloaddition with DACs accompanied by sulfur rearrangement nucleophilic addition/dehydration takes place to give 3-indolyl-4,5-dihydrothiophenes in moderate yields. In addition, the synthetic transformation of 3-indolyl-4,5-dihydrothiophene to sulfone and indole-based axially chiral scaffolds further extends the synthetic utility and structural complexity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"3 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462967","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Synthesis and Performance of l-Tryptophanamide and (S)-1-(Naphthalen-2′-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π–Cation Bonding
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02882
Mariam N. Salib, Tadeusz F. Molinski
{"title":"Synthesis and Performance of l-Tryptophanamide and (S)-1-(Naphthalen-2′-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π–Cation Bonding","authors":"Mariam N. Salib, Tadeusz F. Molinski","doi":"10.1021/acs.joc.4c02882","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02882","url":null,"abstract":"The configurational analysis of amino acids (AAs) in natural product peptides, often containing nonproteinogenic AAs, is mostly carried out by the venerable Marfey’s method using a chiral derivatizing agent (CDA) 1-fluoro-2,4-dinitrophenyl-5-<span>l</span>-alaninamide (<span>l</span>-FDAA)─Marfey’s reagent─which undergoes <i>S</i><sub>N</sub>Ar reaction of the 1° amino group. The resulting AA-DAA derivatives are mostly well-separated by reversed-phase HPLC, but some DAA derivatives resist resolution. Here, we report the synthesis and characterization of two CDAs: <span>l</span>-FDTA (<b>4</b>) in which the <span>l</span>-alanine-derived auxiliary is replaced by <span>l</span>-tryptophanamide and (<i>S</i>)-FDNE (<b>3</b>) where the auxiliary is <i>S</i>-(6-methoxynaphth-2-yl)-1-ethylamine. Side-by-side comparisons of the two reagents were carried out by AA derivatization and reversed-phase HPLC analysis with variables such as organic solvent, additives, and the ionic strength of the mobile phase. <span>l</span>-DTA derivatives of <span>l</span>- and <span>d</span>-AAs were found to show superior HPLC performance and an improvement in resolutions. When incorporated into the mobile phase, the ammonium ion (NH<sub>4</sub><sup>+</sup>, 0–100 mM) showed a dramatic influence on differential retention times [Δ<i>t</i><sub>R</sub> = Δ<i>t</i><sub>R</sub><span>d</span> – Δ<i>t</i><sub>R</sub><span>l</span>] of several key AAs. We attributed the effect to π–cation interactions between the indole ring of DTA and the NH<sub>4</sub><sup>+</sup> counterion in the analyte, a hypothesis supported by <sup>1</sup>H NMR titrations and DFT calculations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Synthesis of Diverse Imidazole and Quinoxaline Derivatives via Iodine-Mediated Cyclization Reactions
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03010
Suganbabu Panneerselvam, Elavarasan Selvaraj, Subramaniyan Mannathan, Thangavelu Saravanan, Baburaj Baskar
{"title":"Synthesis of Diverse Imidazole and Quinoxaline Derivatives via Iodine-Mediated Cyclization Reactions","authors":"Suganbabu Panneerselvam, Elavarasan Selvaraj, Subramaniyan Mannathan, Thangavelu Saravanan, Baburaj Baskar","doi":"10.1021/acs.joc.4c03010","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03010","url":null,"abstract":"A novel approach for the synthesis of diverse substituted imidazoles and quinoxalines via an iodine-promoted cyclization reaction is described. The methodology showcases a broad substrate scope, achieving moderate to very good yields for biologically relevant imidazoles and quinoxalines. Notably, iodine serves as both an iodinating agent and an oxidizing agent, as shown by a mechanistic study. The current methodology is capable of being scaled up to gram quantities, operates in a metal-free environment under mild reaction conditions, and utilizes readily available substrates.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463014","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Nickel-Catalyzed Decarbonylation of Aromatic Carboxylic Acids with P(O)-H(2) Compounds to Form C-P Bonds.
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02554
Jia-Xin Li, Rui Tian, Yong-Ming Zhu
{"title":"Nickel-Catalyzed Decarbonylation of Aromatic Carboxylic Acids with P(O)-H<sub>(2)</sub> Compounds to Form C-P Bonds.","authors":"Jia-Xin Li, Rui Tian, Yong-Ming Zhu","doi":"10.1021/acs.joc.4c02554","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02554","url":null,"abstract":"<p><p>A novel strategy for C-P bond formation has been developed. The reaction employed aromatic carboxylic acids as the source of aromatic groups to couple with three types of P(O)-H<sub>(2)</sub> compounds without the need to isolate intermediates, thereby achieving a one-pot construction of carbon-phosphorus bonds. The protocol demonstrated excellent applicability and functional group tolerance, enabling the production of Ar-P(O)R<sub>2</sub> and Ar<sub>2</sub>-PPh with moderate to excellent yields.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456289","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Synthesis of Indoles through C2–C3 Bond Formation Using Lawesson’s Reagent
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02922
Yao Cheng, Tsz Tin Yu, Mohan Bhadbhade, David StC. Black, Naresh Kumar
{"title":"Synthesis of Indoles through C2–C3 Bond Formation Using Lawesson’s Reagent","authors":"Yao Cheng, Tsz Tin Yu, Mohan Bhadbhade, David StC. Black, Naresh Kumar","doi":"10.1021/acs.joc.4c02922","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02922","url":null,"abstract":"Amidophenylglyoxylic esters react with Lawesson’s reagent at elevated temperatures, leading to the formation of a diverse array of indole derivatives. This methodology demonstrates broad substrate tolerance and utilizes readily available starting materials. Moreover, this synthetic route is metal-free and environmentally compatible. The scalability of this approach is evidenced by successful gram-scale reactions, highlighting its potential industrial applicability. Furthermore, the resulting products are amenable to further modifications, thereby expanding the potential applications of this synthetic strategy.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463013","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Polymer-Supported Selenium Affording Opportunities in Catalyst Design
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c03035
Guangshu Yuan, Xu Zhang, Lei Yu
{"title":"Polymer-Supported Selenium Affording Opportunities in Catalyst Design","authors":"Guangshu Yuan, Xu Zhang, Lei Yu","doi":"10.1021/acs.joc.4c03035","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03035","url":null,"abstract":"Polymer-supported selenium has been reported as a heterogeneous catalyst that is easily separated from the reaction system, thereby making the recovery and reuse of the catalyst more convenient. However, the utilization of polymer-supported selenium in the preparation of catalysts is not restricted to the aforementioned technical advantages. Recent studies have shown that polymer-supported selenium and small-molecule organoselenium catalysts have significant performance differences, leading to distinct reaction mechanisms, which offer more opportunities for the development of new organic reactions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463016","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Mechanistic Insights into the Methylation and Formylation of Amines with CO2: Exploring Diverse CO2 Activation Models.
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1021/acs.joc.4c02854
Pan Du, Ling Han, Xue Zhang, Qin Yu, Li Li, Jiyang Zhao
{"title":"Mechanistic Insights into the Methylation and Formylation of Amines with CO<sub>2</sub>: Exploring Diverse CO<sub>2</sub> Activation Models.","authors":"Pan Du, Ling Han, Xue Zhang, Qin Yu, Li Li, Jiyang Zhao","doi":"10.1021/acs.joc.4c02854","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02854","url":null,"abstract":"<p><p>The urgent need to address global warming and resource depletion has spurred research into sustainable methods for the utilization of CO<sub>2</sub> as a C1 source. However, the challenge remains in developing metal-free, cost-effective, and environmentally friendly approaches for CO<sub>2</sub> conversion. Here, we investigate the mechanisms of CO<sub>2</sub> activation in the methylation and formylation of amines using both theoretical and experimental approaches. Our study reveals that the methylation process is complex, with the \"double H model\" proving most effective, while the formylation reaction is more straightforward, favoring the \"single H model.\" Control experiments confirmed these distinct activation models by monitoring the HCOOH formation. We further evaluated key influencing factors, including Hirshfeld charge and nucleophilicity. Based on our findings, we successfully designed new reactions, demonstrating the practical applications of these mechanisms. This research provides valuable insights into CO<sub>2</sub> conversion strategies, advancing the field of sustainable chemistry.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
The Mechanism of the Cycloaddition of Substituted Ketenes to Cyclopentadiene Based on the Bent Bond/Antiperiplanar Hypothesis Orbital Model.
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1021/acs.joc.4c02083
Mathis Lefebvre, Paul A Johnson, Pierre Deslongchamps
{"title":"The Mechanism of the Cycloaddition of Substituted Ketenes to Cyclopentadiene Based on the Bent Bond/Antiperiplanar Hypothesis Orbital Model.","authors":"Mathis Lefebvre, Paul A Johnson, Pierre Deslongchamps","doi":"10.1021/acs.joc.4c02083","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02083","url":null,"abstract":"<p><p>The [2 + 2] cycloaddition of substituted ketenes with cyclopentadiene producing bicyclo[3.2.0]hept-2-en-6-ones is rationalized by the Bent Bond/Antiperiplanar Hypothesis (BBAH) orbital model. With monosubstituted ketenes, the <i>endo</i> isomer is formed preferentially. The <i>endo</i> and <i>exo</i> isomers are both produced with the cyclobutanone ring in the <b>co-folded in</b> conformation. Computational results support the analysis of the BBAH based mechanism in agreement with experimental results.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447495","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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