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Constructing chiral bicyclo[3.2.1]octanes via low-loading organocatalysis. 低负荷有机催化构建手性双环[3.2.1]辛烷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-06 DOI: 10.1039/d5ob00203f
Etikala Ashok, Pandhiti R Lakshmi, Revoju Sravanthi, Dhevalapally B Ramachary
{"title":"Constructing chiral bicyclo[3.2.1]octanes <i>via</i> low-loading organocatalysis.","authors":"Etikala Ashok, Pandhiti R Lakshmi, Revoju Sravanthi, Dhevalapally B Ramachary","doi":"10.1039/d5ob00203f","DOIUrl":"https://doi.org/10.1039/d5ob00203f","url":null,"abstract":"<p><p>Multi-centric ambident 2-hydroxy-3,5-dialkyl-<i>p</i>-quinones selectively reacted with α-alkylnitroethylenes under a low-loading of (1.0 mol% to 500 ppm) Rawal's quinine-squaramide-catalyst, followed by <i>in situ</i> acid-catalysed <i>tert</i>-hydroxy group acetylation to construct high-yielding chiral bicyclo[3.2.1]octanes in up to single dr and er through [3 + 2]-annulations under ambient conditions. These kinds of rare low organocatalyst-loading, asymmetric, one-pot, gram-scale annulations will be highly inspirational to plan a greater number of low-loading organocatalytic asymmetric reactions in both academia and industry. Additionally, bicyclo[3.2.1]octanes are basic skeletons of many natural products and drugs, which highlights the importance of developing the present catalytic asymmetric protocol for the synthesis of both achiral and chiral versions of functionally rich bicyclo[3.2.1]octanes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952610","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
Substrate- and reagent-dependent selective annulation of amidines and 2-tert-amino benzaldehydes† 底物和试剂依赖的脒和2-叔氨基苯甲醛的选择性环化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-05 DOI: 10.1039/D5OB00424A
Yi Zhang, Renchao Ma, Yongmin Ma and Weiwei Fang
{"title":"Substrate- and reagent-dependent selective annulation of amidines and 2-tert-amino benzaldehydes†","authors":"Yi Zhang, Renchao Ma, Yongmin Ma and Weiwei Fang","doi":"10.1039/D5OB00424A","DOIUrl":"10.1039/D5OB00424A","url":null,"abstract":"<p >Herein, we present an efficient and substrate/reagent-dependent annulation of amidines with 2-<em>tert</em>-amino benzaldehydes. When <em>N</em>-alkyl benzimidamides are employed, amidines undergo self-annulation to generate a hydrotriazine skeleton. In contrast, <em>N</em>-aryl benzimidamides yield quinazolines/hydroquinazolines under similar conditions. Additionally, the coupling of 2-<em>tert</em>-amino benzaldehydes with amidines under basic conditions yields 1,3,5-triazine derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5111-5115"},"PeriodicalIF":2.9,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952202","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 catalysts supported on phosphorus-rich covalent organic polymers for sustainable hydrosilylation of alkynes† 富磷共价有机聚合物负载铑催化剂用于炔烃可持续硅氢化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-05 DOI: 10.1039/D5OB00462D
Xin Liu, Xinxin Han, Jiaxi Cai, Qiaoya Wang, Aizhao Pan and Mingyou Hu
{"title":"Rhodium catalysts supported on phosphorus-rich covalent organic polymers for sustainable hydrosilylation of alkynes†","authors":"Xin Liu, Xinxin Han, Jiaxi Cai, Qiaoya Wang, Aizhao Pan and Mingyou Hu","doi":"10.1039/D5OB00462D","DOIUrl":"10.1039/D5OB00462D","url":null,"abstract":"<p >Heterogeneous rhodium catalysts supported on phosphorus-rich covalent organic polymers provide a sustainable solution to the scarcity of Rh resources in the chemical industry. We synthesized COP-PPh<small><sub>3</sub></small> by utilizing triphenylphosphine as monomers and then supported rhodium on COP-PPh<small><sub>3</sub></small> to generate the heterogeneous Rh catalyst COP-PPh<small><sub>3</sub></small>-RhCl. This catalyst demonstrated excellent catalytic activity and substrate adaptability in alkyne hydrosilylation reactions. Even after five reuse cycles, COP-PPh<small><sub>3</sub></small>-RhCl maintained high catalytic activity and structural stability, with consistent Rh loading amounts. This approach effectively addresses challenges related to recycling and reusing homogeneous precious metal catalysts, offering a promising strategy to alleviate precious metal scarcity and reduce environmental pollution risks.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5208-5214"},"PeriodicalIF":2.9,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955618","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
Palindromic peptide foldamers: a strategy for structural stability and cellular uptake. 回文肽折叠体：结构稳定性和细胞摄取的策略。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-02 DOI: 10.1039/d5ob00430f
Minami Fujita, Takahito Ito, Akihiko Inokuma, Kosuke Saito, Motoharu Hirano, Hidetomo Yokoo, Yosuke Demizu
{"title":"Palindromic peptide foldamers: a strategy for structural stability and cellular uptake.","authors":"Minami Fujita, Takahito Ito, Akihiko Inokuma, Kosuke Saito, Motoharu Hirano, Hidetomo Yokoo, Yosuke Demizu","doi":"10.1039/d5ob00430f","DOIUrl":"https://doi.org/10.1039/d5ob00430f","url":null,"abstract":"<p><p>Mid-sized peptide therapeutics have gained significant attention for their potential to overcome the limitations of small molecules and biologics. However, their clinical application is often hindered by poor stability and low cellular permeability. In this study, we designed a palindromic peptide foldamer composed of L-leucine and L-arginine residues to investigate its structural and functional properties. CD spectroscopy confirmed that the designed peptide adopts a stable α-helical conformation, even under denaturing conditions. Cellular uptake studies using LC-MS/MS and flow cytometry indicated efficient intracellular delivery, suggesting that the peptide's amphiphilic structure enhances membrane permeability. These findings provide valuable insights into the rational design of structurally stable and functionally enhanced peptide therapeutics.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951924","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
Chemical modification of sialylated oligosaccharides to functionalize nanostructured lipid carriers: exploring two different strategies† 唾液化低聚糖的化学修饰使纳米结构脂质载体功能化：探索两种不同的策略。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-30 DOI: 10.1039/D5OB00270B
Paul Rivollier, Emeline Richard, Antoine Hoang, Aurélien Traversier, Manuel Rosa-Calatrava, Dorothée Jary, Isabelle Texier and Sébastien Fort
{"title":"Chemical modification of sialylated oligosaccharides to functionalize nanostructured lipid carriers: exploring two different strategies†","authors":"Paul Rivollier, Emeline Richard, Antoine Hoang, Aurélien Traversier, Manuel Rosa-Calatrava, Dorothée Jary, Isabelle Texier and Sébastien Fort","doi":"10.1039/D5OB00270B","DOIUrl":"10.1039/D5OB00270B","url":null,"abstract":"<p >Nanostructured lipid carriers (NLCs) are innovative lipid-based formulations made up of a carefully balanced mixture of solid and liquid lipids in their core. This unique architecture offers several advantages over traditional lipid nanoparticles, including enhanced stability and improved drug loading capacity. NLC nanoparticles hold great promise across various sectors, including pharmaceuticals, healthcare, dietary supplements, functional foods and beverages, as well as cosmetics and personal care products. To enhance the targeting capabilities of these nanoparticles, their surface must be functionalized with biomolecules to support specific interactions with biological receptors. Here, we compared two synthesis strategies for functionalizing the surface of NLCs with <em>N</em>-acetyl-neuraminic acid (Neu5Ac), a major carbohydrate involved in many cellular functions. 6′- and 3′-Sialyllactose were enzymatically produced and directly functionalized on their reducing ends using either oxime ligation or reductive amination. In the first strategy, thiol-modified oligosaccharides were grafted onto maleimide-decorated NLCs, and the second strategy focused on incorporating sialylated glycolipids into the formulation. Both methods successfully produced stable and monodisperse nanoparticles with sizes ranging from 60 to 100 nm. The functionalization efficiency (46 to 86%) was assessed by quantifying Neu5Ac present at the particle surface. The grafting approach yielded safe nanoparticles that show potential for use in anti-adhesive therapies against pathogens, such as the influenza viruses. However, their effectiveness needs to be optimized by further increasing carbohydrate density on the nanoparticle surface.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5240-5250"},"PeriodicalIF":2.9,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143957290","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
Photocatalytic three-component reaction for synthesis of dithio-carbamates† 光催化三组分反应合成二硫代氨基甲酸酯。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-30 DOI: 10.1039/D5OB00489F
Xin-Yu Mei, Hui-Ling Lu, Shi-Long Zhong, Bo-Jiang Chen, Zi-Wei Xi, Qiliang Yuan and Yong-Miao Shen
{"title":"Photocatalytic three-component reaction for synthesis of dithio-carbamates†","authors":"Xin-Yu Mei, Hui-Ling Lu, Shi-Long Zhong, Bo-Jiang Chen, Zi-Wei Xi, Qiliang Yuan and Yong-Miao Shen","doi":"10.1039/D5OB00489F","DOIUrl":"10.1039/D5OB00489F","url":null,"abstract":"<p >This manuscript describes a visible light induced photocatalytic three-component reaction of an alkyl halide ([(iodomethyl) sulfonyl] benzene or arylmethyl bromide), carbon disulfide, and amine for the synthesis of dithiocarbamates under mild conditions. Sulfonyl dithiocarbamates were synthesized within 30 minutes without the need for any catalysts and additives. The reaction is characterized by high efficiency, wide substrate scope, a green catalyst-free protocol, and the easiness for scale-up. A possible reaction mechanism was suggested on the basis of free radical trapping and UV absorption spectroscopy experiment.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5197-5202"},"PeriodicalIF":2.9,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143958825","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
Synthesis of dihydropyrimidinones via urea-based multicomponent reactions 脲基多组分反应合成二氢嘧啶类化合物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-29 DOI: 10.1039/D5OB00180C
Anirban Mandal, Prasanjit Ghosh and Sajal Das
{"title":"Synthesis of dihydropyrimidinones via urea-based multicomponent reactions","authors":"Anirban Mandal, Prasanjit Ghosh and Sajal Das","doi":"10.1039/D5OB00180C","DOIUrl":"10.1039/D5OB00180C","url":null,"abstract":"<p >Multicomponent reactions (MCRs) have emerged as powerful tools in organic chemistry, enabling the rapid and efficient assembly of complex molecular architectures. Urea-based multicomponent reactions have gained significant attention due to their versatility and broad applicability. In this review, we highlight recent developments in this area, with a focus on dihydropyrimidinones, and provide an in-depth analysis of the diverse synthetic pathways and applications of urea-based MCRs, shedding light on their fundamental mechanisms, reaction conditions, and potential for green and sustainable synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5064-5080"},"PeriodicalIF":2.9,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955858","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
Metal-free, visible-light-mediated phototransformations of ortho-biaryl appended chalcones: access to oxathia[5]helicenes and 1,2,3,4-tetrasubstituted cyclobutanes† 邻联芳基附加查尔酮的无金属、可见光介导的光转化：获得草酸[5]螺旋烯和1,2,3,4-四取代环丁烷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-29 DOI: 10.1039/D5OB00490J
A. V. Zakharov, E. E. Evsikova, P. D. Grebennikova, M. A. Krylova, A. N. Fakhrutdinov and V. Z. Shirinian
{"title":"Metal-free, visible-light-mediated phototransformations of ortho-biaryl appended chalcones: access to oxathia[5]helicenes and 1,2,3,4-tetrasubstituted cyclobutanes†","authors":"A. V. Zakharov, E. E. Evsikova, P. D. Grebennikova, M. A. Krylova, A. N. Fakhrutdinov and V. Z. Shirinian","doi":"10.1039/D5OB00490J","DOIUrl":"10.1039/D5OB00490J","url":null,"abstract":"<p >Visible-light-mediated metal-free irreversible phototransformations of <em>ortho</em>-bihetaryl appended chalcones are reported. Isosteric replacement of one of the aryl residues with a chalcone fragment in diarylethene (terarylene) molecules leads to a significant expansion of the synthetic capabilities of these compounds, thereby opening up access to a wide range of new functional materials. It was found for the first time that protonation of the carbonyl group in the chalcone moiety of <em>ortho</em>-bihetarylchalcones exclusively promotes 6π-photocyclization leading to the formation of oxathia[5]helicenes, whereas 1,2,3,4-tetrasubstituted cyclobutanes are preferably formed upon photolysis in toluene in the presence of triethylamine. The formation of the helicene framework is due to visible light-induced 6π-electrocyclization of the hexatriene system of bihetaryl chalcones, and [2 + 2]-photocycloaddition is facilitated by the aggregation of chalcone molecules, which is a consequence of the formation of a head-to-head excimer due to π–π-stacking interactions of naphthofuran polyaromatic systems. These results will provide valuable information on the photocyclization of new diarylethene analogues, which can be used to develop new efficient protocols for the synthesis of fused heteroaromatic frameworks and promising materials with wide applications in material science, molecular electronics and medicine.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5182-5190"},"PeriodicalIF":2.9,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953311","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
Silver-catalyzed generation of acyl radicals from α-imino-oxy acids: access to acylated 3-CF3-2-oxindoles† 银催化α-亚胺氧酸生成酰基自由基：获得酰基化的3- cf3 -2-氧吲哚。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-29 DOI: 10.1039/D5OB00262A
Yating Cao, Yushan Wei, Yingxin Hu, Daosheng Liu, Mengyao Liu, Jingjing Wang, Chong Li, Pinpin Wang, Liyan Hu and Feng Li
{"title":"Silver-catalyzed generation of acyl radicals from α-imino-oxy acids: access to acylated 3-CF3-2-oxindoles†","authors":"Yating Cao, Yushan Wei, Yingxin Hu, Daosheng Liu, Mengyao Liu, Jingjing Wang, Chong Li, Pinpin Wang, Liyan Hu and Feng Li","doi":"10.1039/D5OB00262A","DOIUrl":"10.1039/D5OB00262A","url":null,"abstract":"<p >A unified strategy to generate acyl radicals from α-imino-oxy acids <em>via</em> selective C–C bond activation is reported. In the presence of a silver catalyst, α-imino-oxy acids could undergo decarboxylation and N–O and C–C bond homolysis to deliver the acyl radicals, which were subsequently captured by <em>N</em>-alkyl-<em>N</em>-aryl-2-(trifluoromethyl)acrylamides to access acylated 3-CF<small><sub>3</sub></small>-2-oxindoles.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5106-5110"},"PeriodicalIF":2.9,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955460","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
Correction: Computational methods for investigating organic radical species
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-29 DOI: 10.1039/D5OB90053K
Tim Renningholtz, Ethan R. X. Lim, Michael J. James and Cristina Trujillo
{"title":"Correction: Computational methods for investigating organic radical species","authors":"Tim Renningholtz, Ethan R. X. Lim, Michael J. James and Cristina Trujillo","doi":"10.1039/D5OB90053K","DOIUrl":"https://doi.org/10.1039/D5OB90053K","url":null,"abstract":"<p >Correction for ‘Computational methods for investigating organic radical species’ by Tim Renningholtz <em>et al.</em>, <em>Org. Biomol. Chem.</em>, 2024, <strong>22</strong>, 6166–6173, https://doi.org/10.1039/D4OB00532E.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 19","pages":" 4794-4794"},"PeriodicalIF":2.9,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob90053k?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143944156","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
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