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Fujiwara-Moritani reaction: challenges and new opportunities 藤原-森谷反应：挑战与新机遇
Tetrahedron chem Pub Date : 2025-04-18 DOI: 10.1016/j.tchem.2025.100130
Xiaojian Chen , Jun Zhang , Yang Gao, Qian Chen, Yanping Huo, Xianwei Li
{"title":"Fujiwara-Moritani reaction: challenges and new opportunities","authors":"Xiaojian Chen ,&nbsp;Jun Zhang ,&nbsp;Yang Gao,&nbsp;Qian Chen,&nbsp;Yanping Huo,&nbsp;Xianwei Li","doi":"10.1016/j.tchem.2025.100130","DOIUrl":"10.1016/j.tchem.2025.100130","url":null,"abstract":"<div><div>Fujiwara-Moritani reaction has proven to be robust for the efficient construction of polyfunctionalized olefins and cyclic skeletons. Recent advances toward greener systems, compatibility with strongly coordinating heterocycle substrates and sterically hindered internal olefins, and achieving asymmetric catalysis have collectively opened new frontiers for Fujiwara-Moritani reaction.2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100130"},"PeriodicalIF":0.0,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143860532","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoinduced enantioselective transformations via o-quinodimethane intermediates 通过邻喹诺二甲烷中间体的光诱导对映选择性转化
Tetrahedron chem Pub Date : 2025-04-16 DOI: 10.1016/j.tchem.2025.100131
Liwen Xia , Qingqin Huang , Zhao-Fei Zhang , Lei Dai
{"title":"Photoinduced enantioselective transformations via o-quinodimethane intermediates","authors":"Liwen Xia ,&nbsp;Qingqin Huang ,&nbsp;Zhao-Fei Zhang ,&nbsp;Lei Dai","doi":"10.1016/j.tchem.2025.100131","DOIUrl":"10.1016/j.tchem.2025.100131","url":null,"abstract":"<div><div>The effective stereoselective control of transient intermediates remains a formidable challenge in synthetic chemistry. <em>o</em>-Quinodimethane generated by photo-irradation has been extensively investigated and widely utilized as a nucleophilic surrogate. Nevertheless, enantioselective transformations involving <em>o</em>-quinodimethane are still underdeveloped, due to the persistent challenges in intercepting these intermediates and achieving effective stereoselective control with chiral catalysts. In this review, we summarize recent advances in photoinduced enantioselective reactions of <em>o</em>-quinodimethane, highlighting catalytic strategies, mechanistic insights, and current limitations in the field.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100131"},"PeriodicalIF":0.0,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847937","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes 镍催化通过烯基硅烷的卤代氟烷基化和氢氟烷基化合成含氟硅烷
Tetrahedron chem Pub Date : 2025-04-14 DOI: 10.1016/j.tchem.2025.100129
Ting Su , Heng Wang , Wenxin Lu , Wei Huang , Qinglei Chong , Fanke Meng
{"title":"Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes","authors":"Ting Su ,&nbsp;Heng Wang ,&nbsp;Wenxin Lu ,&nbsp;Wei Huang ,&nbsp;Qinglei Chong ,&nbsp;Fanke Meng","doi":"10.1016/j.tchem.2025.100129","DOIUrl":"10.1016/j.tchem.2025.100129","url":null,"abstract":"<div><div>Fluorine-bearing silanes have displayed widespread applications in organic synthesis and inorganic and material chemistry due to their high reactivity and versatility. However, the synthesis of fluorine-containing compounds featuring a difluorine-bearing silane is still underdeveloped. Here, we reported a simple, mild and efficient method for halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes with bromodifluoroacetates under nickel catalysis, affording a variety of fluorine-bearing silanes in up to 89 % yield. This research was distinguished by its good functional group tolerance, moderate to good yields and exclusive regioselectivity.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100129"},"PeriodicalIF":0.0,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143843361","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs 自由基SAM环烷合成酶催化在多个trp基序上形成均匀的环烷
Tetrahedron chem Pub Date : 2025-03-27 DOI: 10.1016/j.tchem.2025.100128
Abujunaid Habib Khan , Jabal Rahmat Haedar , Anitra Zīle , Chin-Soon Phan
{"title":"Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs","authors":"Abujunaid Habib Khan ,&nbsp;Jabal Rahmat Haedar ,&nbsp;Anitra Zīle ,&nbsp;Chin-Soon Phan","doi":"10.1016/j.tchem.2025.100128","DOIUrl":"10.1016/j.tchem.2025.100128","url":null,"abstract":"<div><div>Cyclophane-containing products from ribosomally synthesized and post-translationally modified peptides (RiPPs) are generated by radical SAM cyclophane synthases (rSAM). In the past few years, rSAM enzymes that catalyze uniform cyclophanes at multiple Trp-motifs on the precursor peptides have been discovered more frequently. These enzymes install C–C or C–O cross-links at the three-residue motifs between Trp-C5/C6/C7 and an <em>sp</em><sup>3</sup> carbon side chain to generate strained macrocycles. This mini-review will focus on the rSAM enzymes, WprB, OscB, XncB, FwwB and RscB to summarize the biosynthesis and NMR characterization of Trp-containing cyclophane products, and promiscuity of these enzymes.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100128"},"PeriodicalIF":0.0,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738802","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total synthesis of the assigned structure of (+)-Maneolactenol （+）-马油酸醇配位结构的全合成
Tetrahedron chem Pub Date : 2025-03-13 DOI: 10.1016/j.tchem.2025.100127
Yidong Huang , Weiwu Ren
{"title":"Total synthesis of the assigned structure of (+)-Maneolactenol","authors":"Yidong Huang ,&nbsp;Weiwu Ren","doi":"10.1016/j.tchem.2025.100127","DOIUrl":"10.1016/j.tchem.2025.100127","url":null,"abstract":"<div><div>The first total synthesis of the assigned structure of (+)-maneolactenol, a marine natural product, has been completed in 7 steps. The pivotal transformations involve an asymmetric Diels-Alder reaction which serves as a key step in establishing stereochemistry, and the formation of core skeleton through iodolactonization. Particularly noteworthy are the selective reduction of acid to aldehyde and subsequent chelation-controlled stereoselective nucleophilic addition, facilitating the rapid and efficient assembly of side-chain motifs, as well as the selective reduction of the triple bond to <em>Z</em>-olefin moiety for the side chain construction. This strategy enabled the scalable synthesis of over 100 mg of the target compound, highlighting its practicality for larger-scale production.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100127"},"PeriodicalIF":0.0,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628787","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in electrochemical deoxygenative functionalization of alcohols and their derivatives 醇及其衍生物电化学脱氧官能化的最新进展
Tetrahedron chem Pub Date : 2025-03-12 DOI: 10.1016/j.tchem.2025.100126
Yong Yuan, Lili Liu, Feng Zhang, Ya-Nan Zhang, Congde Huo
{"title":"Recent advances in electrochemical deoxygenative functionalization of alcohols and their derivatives","authors":"Yong Yuan,&nbsp;Lili Liu,&nbsp;Feng Zhang,&nbsp;Ya-Nan Zhang,&nbsp;Congde Huo","doi":"10.1016/j.tchem.2025.100126","DOIUrl":"10.1016/j.tchem.2025.100126","url":null,"abstract":"<div><div>This mini-review discusses the recent breakthroughs for electrochemical deoxygenative functionalization of alcohols and their derivatives. A diverse range of deoxygenative transformations is described, including the deoxygenative arylation, heteroarylation, alkylation, allylation, hydrogenation, cyanation, amination, borylation, and carboxylation. We hope that this mini-review can promote the rapid development in the field of electrochemical deoxygenative functionalization of alcohols and their derivatives.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100126"},"PeriodicalIF":0.0,"publicationDate":"2025-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143620354","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient workflow for structural elucidation applied to solidagenone derivative: Combining the speed of ML-J-DP4 screening with the precision of DP4+ 高效的solidagenone衍生物结构解析工作流程：结合ML-J-DP4筛选的速度和DP4+的精度
Tetrahedron chem Pub Date : 2025-03-06 DOI: 10.1016/j.tchem.2025.100125
Iván Cortés , María Luz Tibaldi-Bollati , Viviana E. Nicotra , Manuela E. García , Ariel M. Sarotti
{"title":"Efficient workflow for structural elucidation applied to solidagenone derivative: Combining the speed of ML-J-DP4 screening with the precision of DP4+","authors":"Iván Cortés ,&nbsp;María Luz Tibaldi-Bollati ,&nbsp;Viviana E. Nicotra ,&nbsp;Manuela E. García ,&nbsp;Ariel M. Sarotti","doi":"10.1016/j.tchem.2025.100125","DOIUrl":"10.1016/j.tchem.2025.100125","url":null,"abstract":"<div><div>The derivatization of solidagenone through ring expansion, using the \"Complexity to Diversity\" synthetic strategy to obtain polyketones, yielded two products upon reaction of an intermediate with <em>in situ-</em>generated ruthenium tetroxide. As might happen, the spectroscopic and spectrometric data were inconclusive for the structural determination of one of these products. To address the issue, a ML-<em>J</em>-DP4//DP4+ workflow was studied, which allowed simultaneous determination of connectivity and relative configuration with high accuracy, while saving computational resources. Furthermore, during the calculation of NMR data at the DP4+ level, abnormally large errors were observed for the beta carbon of a polyhydroxylated conjugated enone. A literature analysis revealed that this behavior could be generalized, and after careful examination, it was determined to be the result of small geometric distortions caused by an overestimated network of intramolecular hydrogen bonds. To mitigate this common source of discrepancy, a heuristic solution was introduced as a proof of concept by <em>in silico</em> blocking of hydroxyl groups.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100125"},"PeriodicalIF":0.0,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation nhc催化heck型C-H叔烷基化构建全碳季中心
Tetrahedron chem Pub Date : 2025-03-01 DOI: 10.1016/j.tchem.2025.100124
Tinglan Liu , Pan Yue , Chengming Wang
{"title":"Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation","authors":"Tinglan Liu ,&nbsp;Pan Yue ,&nbsp;Chengming Wang","doi":"10.1016/j.tchem.2025.100124","DOIUrl":"10.1016/j.tchem.2025.100124","url":null,"abstract":"<div><div>A variety of alkylated alkenes with all-carbon quaternary centers were regioselectively accessed by Heck-type radical NHC catalysis. The herein-developed methodology may contribute to the efficient and rapid construction of various pharmaceuticals and natural products.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100124"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143619107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal-free sulfenylation of pyrrolo[1,2-a]quinoxaline with diaryl disulfide facilitated by TBATB TBATB催化吡咯[1,2-a]喹啉与二硫酰基的无金属磺化反应
Tetrahedron chem Pub Date : 2025-01-24 DOI: 10.1016/j.tchem.2025.100123
Yingqian Li, Yali Liu, Yan Liu, Xiaowei Ma, Liang Xu, Ping Liu
{"title":"Metal-free sulfenylation of pyrrolo[1,2-a]quinoxaline with diaryl disulfide facilitated by TBATB","authors":"Yingqian Li,&nbsp;Yali Liu,&nbsp;Yan Liu,&nbsp;Xiaowei Ma,&nbsp;Liang Xu,&nbsp;Ping Liu","doi":"10.1016/j.tchem.2025.100123","DOIUrl":"10.1016/j.tchem.2025.100123","url":null,"abstract":"<div><div>A direct metal-free C1–H sulfenylation reaction of pyrrolo[1,2-<em>a</em>]quinoxaline with diaryl disulfides was developed at 50 °C using tetrabutylammonium tribromide (TBATB) as a promoter. Notably, raising the reaction temperature to 100 °C, TBATB played the dual role of both promoter and reactant, resulting in the simultaneous formation of C1–S bond and C3–Br bonds. The protocol has mild reaction conditions, broad substrate scope and good chemical and regioselectivity. In addition, the bifunctionalized reaction can be carried out smoothly at a gram-scale level, enabling the synthesis of structurally diverse pyrrolo[1,2-<em>a</em>]quinoxaline compounds.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100123"},"PeriodicalIF":0.0,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182683","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 novel benzo fused bridged azaheterocycles through the reaction of chalcone with hydrazone 通过查尔酮与腙的反应合成新型苯并熔桥氮杂环
Tetrahedron chem Pub Date : 2025-01-23 DOI: 10.1016/j.tchem.2025.100122
Congyang Li , Ruochen Pang , Weiwu Ren
{"title":"Synthesis of novel benzo fused bridged azaheterocycles through the reaction of chalcone with hydrazone","authors":"Congyang Li ,&nbsp;Ruochen Pang ,&nbsp;Weiwu Ren","doi":"10.1016/j.tchem.2025.100122","DOIUrl":"10.1016/j.tchem.2025.100122","url":null,"abstract":"<div><div>We reported a direct construction of aza-[3.3.1]-bicycles from 2-aminochalcones and hydrazone. Notably, this method formed a potentially biologically active bridged structure containing multiple nitrogen atoms under mild conditions with high yields. This reaction exhibits broad substrate scope and excellent functional group tolerance. This is a new type of benzo fused bridged azaheterocycles, which will be beneficial for further research on this skeleton.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100122"},"PeriodicalIF":0.0,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182682","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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