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Bromotrifluoromethoxylation of allenes: expedient access to allylic trifluoromethoxy derivatives† 烯基溴三氟甲氧基化：丙烯基三氟甲氧基衍生物的一种权宜之计
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d4qo02426e
Rui Liu , Yangdong Hou , Pingping Tang
{"title":"Bromotrifluoromethoxylation of allenes: expedient access to allylic trifluoromethoxy derivatives†","authors":"Rui Liu ,&nbsp;Yangdong Hou ,&nbsp;Pingping Tang","doi":"10.1039/d4qo02426e","DOIUrl":"10.1039/d4qo02426e","url":null,"abstract":"<div><div>A mild and efficient method for the bromotrifluoromethoxylation of allenes has been explored using trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxy source. A series of allylic trifluoromethoxy derivatives were obtained with high yields and good regioselectivity by terminal selectivity of the allenes. This transition metal-free process expands the scope of the application of trifluoromethoxy reagents.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3960-3964"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143672300","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
An efficient total synthesis of (+)-entecavir† （+）-恩替卡韦的高效全合成
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00329f
Chenlong Zhu , Nanlian Li , Yaopeng Ma , Bingfeng Sun
{"title":"An efficient total synthesis of (+)-entecavir†","authors":"Chenlong Zhu ,&nbsp;Nanlian Li ,&nbsp;Yaopeng Ma ,&nbsp;Bingfeng Sun","doi":"10.1039/d5qo00329f","DOIUrl":"10.1039/d5qo00329f","url":null,"abstract":"<div><div>An efficient asymmetric total synthesis of entecavir was accomplished in 9 steps from the commercially available 4-hydroxycyclopent-2-enone (<em>rac</em>-), representing, to date, the shortest asymmetric total synthesis of this molecule. Key reactions include a lipase-mediated highly efficient kinetic resolution reaction and a highly challenging stereocontrolled copper-catalyzed Michael addition–elimination reaction. This work constitutes a robust basis for the development of a new step-economic and cost-effective process for the production of entecavir.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4045-4049"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758575","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
Copper-mediated divergent synthesis of halogenated 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes and α,α-dibromo imines from N-allyl enamines† 铜介导N -烯丙基烯胺发散合成卤代1-吡咯、3-阿扎比环[3.1.0]己二烯和α， α-二溴亚胺
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00217f
Xiyan Duan , Junqi Wang , Kun Liu , Fengjiao Du , Maoling He , Wenxin Li , Xinming Liu , Pu Liu
{"title":"Copper-mediated divergent synthesis of halogenated 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes and α,α-dibromo imines from N-allyl enamines†","authors":"Xiyan Duan ,&nbsp;Junqi Wang ,&nbsp;Kun Liu ,&nbsp;Fengjiao Du ,&nbsp;Maoling He ,&nbsp;Wenxin Li ,&nbsp;Xinming Liu ,&nbsp;Pu Liu","doi":"10.1039/d5qo00217f","DOIUrl":"10.1039/d5qo00217f","url":null,"abstract":"<div><div>By varying the halide type and its addition rate, the divergent synthesis of dibromo 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes, and α,α-dibromo imines from <em>N</em>-allyl enamines was successfully achieved. 1-Pyrrolines and 3-azabicyclo[3.1.0]hex-2-enes are important building blocks in organic synthesis and pharmaceutical chemistry. Herein, we disclose a chemodivergent protocol for the Cu-mediated, halide-controlled annulation of <em>N</em>-allyl enamines, enabling straightforward access to these valuable scaffolds with good yields and high selectivity. The type of halogen reagent, its addition rate, and the solvent are critical for controlling reaction selectivity. A reaction mechanism is proposed, which involves X-transfer/radical cyclization to construct pyrrolines or 3-azabicyclo[3.1.0]hex-2-enes. It is worth mentioning that <em>N</em>-allyl enamine serves as both a bromine acceptor and donor in this transformation. This strategy employs readily available starting materials, mild conditions, and a simple protocol and exhibits good functional group compatibility, demonstrating that <em>N</em>-allyl enamines are versatile building blocks for constructing nitrogen-containing heterocycles.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4012-4017"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734059","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
Steroidal sapogenin-derived chirons: underdeveloped building blocks with methyl-branched chiral centers 甾体皂苷元衍生的手性：具有甲基支化手性中心的不发达的构建块
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00090d
Yu-Chuan Pu , Gen-Ying Liu , Ran Gao , Cheng-Yu He
{"title":"Steroidal sapogenin-derived chirons: underdeveloped building blocks with methyl-branched chiral centers","authors":"Yu-Chuan Pu ,&nbsp;Gen-Ying Liu ,&nbsp;Ran Gao ,&nbsp;Cheng-Yu He","doi":"10.1039/d5qo00090d","DOIUrl":"10.1039/d5qo00090d","url":null,"abstract":"<div><div>Three kinds of chiral lactones with methyl-branched stereocenters were obtained on large scale based on H<sub>2</sub>O<sub>2</sub>-mediated oxidative degradation of steroidal sapogenins. These chiral lactones are valuable chirons for the total synthesis of bioactive compounds containing methyl-branched chiral centers. This review comprehensively summarizes the synthetic application of the steroidal sapogenin-derived chiral lactones in insect pheromones, complex natural products and pharmaceuticals, with a particular focus on the chirality transfer from chiral lactones to the corresponding motifs of target molecules. We hope these underdeveloped chirons can act as a complement to commonly used methyl-branched chirons such as citronellol and Roche ester, and meet more synthetic applications in the future.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4181-4194"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143675177","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
Solvent-controlled 4CzBnBN-catalyzed intramolecular photocyclization and dehydrogenative photocyclization of indole carboxamides for the switchable synthesis of indoloquinolones and dihydroindoloquinolones† 溶剂控制4czbnbn催化吲哚羧基酰胺分子内光环化和脱氢光环化合成吲哚喹诺酮类和二氢吲哚喹诺酮类化合物
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00185d
Yihao Zhang , Peng Zhang , Hang Zhao , Xing Wang , Xia Zhou , Yimou Gong , Lin Wang , Siping Wei , Zhijie Zhang , Qiang Fu
{"title":"Solvent-controlled 4CzBnBN-catalyzed intramolecular photocyclization and dehydrogenative photocyclization of indole carboxamides for the switchable synthesis of indoloquinolones and dihydroindoloquinolones†","authors":"Yihao Zhang ,&nbsp;Peng Zhang ,&nbsp;Hang Zhao ,&nbsp;Xing Wang ,&nbsp;Xia Zhou ,&nbsp;Yimou Gong ,&nbsp;Lin Wang ,&nbsp;Siping Wei ,&nbsp;Zhijie Zhang ,&nbsp;Qiang Fu","doi":"10.1039/d5qo00185d","DOIUrl":"10.1039/d5qo00185d","url":null,"abstract":"<div><div>Indoloquinolones and dihydroindoloquinolones are in-demand motifs in medicinal chemistry, yet methods for the controlled synthesis of both molecules are scarce. We detail the solvent-controlled switchable photocyclization and dehydrogenative photocyclization of heterocyclic anilides for the rapid and divergent synthesis of indoloquinolinones and dihydroindoloquinolinones. By using 4CzBnBN and DCM/MeOH as the catalytic system, a photocyclization reaction is achieved with excellent diastereoselectivity and good yields, resulting in the <em>cis</em>-selective synthesis of dihydroindoloquinolinones exclusively. Upon changing the solvent to DCE/DMSO, the reaction pathways switch to dehydrogenative photocyclization that provided indoloquinolinones. The success of this reaction hinges on the photophysical properties of the photocatalyst and its combination with specific solvents. Mechanistic studies including Stern–Volmer quenching studies, isotope labeling experiments, Volhard titration methods and DFT calculations have revealed that an energy transfer process is involved in the photocyclization reaction, while both energy transfer and electron transfer processes occur during the dehydrogenative photocyclization reaction. Our research not only provides a novel strategy for the synthesis of medicinally intriguing molecules of indoloquinolinones and dihydroindoloquinolinones but also offers insights into the modulation of catalytic performance of cyanocarbazole-based catalysts.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3976-3983"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734061","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
Fe-Catalyzed B–H and N–H insertion reactions of iodonium ylides† 铁催化碘化物的B-H和N-H插入反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d4qo01916d
Hejun An , Zhi Cui , Jinchao Liang , Xingxing Ma , Jinglong Chen , Qiuling Song
{"title":"Fe-Catalyzed B–H and N–H insertion reactions of iodonium ylides†","authors":"Hejun An ,&nbsp;Zhi Cui ,&nbsp;Jinchao Liang ,&nbsp;Xingxing Ma ,&nbsp;Jinglong Chen ,&nbsp;Qiuling Song","doi":"10.1039/d4qo01916d","DOIUrl":"10.1039/d4qo01916d","url":null,"abstract":"<div><div>Herein, B–H and N–H insertion reactions of iodonium ylides in the presence of an iron catalyst complexed with imidazo[1,5-<em>a</em>]pyridine are developed, achieving the borylation and amination of 1,3-dicarbonyl derivatives under mild reaction conditions. Mechanistic investigations show that an iron carbene is involved in this process. Besides, this reaction features high efficiency, a broad substrate scope and good functional group tolerance, and propionate ester scaffolds can be introduced into various drug molecules <em>via</em> this protocol.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4058-4065"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723999","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
NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes† NHC和光氧化还原共催化1,3-炔的1,4-烷基羰基化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d4qo02311k
Zhaoyang Zhang , Jia-Yi Yang , Shihao Li , Xiao-Xuan Li , Yi-Si Feng
{"title":"NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes†","authors":"Zhaoyang Zhang ,&nbsp;Jia-Yi Yang ,&nbsp;Shihao Li ,&nbsp;Xiao-Xuan Li ,&nbsp;Yi-Si Feng","doi":"10.1039/d4qo02311k","DOIUrl":"10.1039/d4qo02311k","url":null,"abstract":"<div><div>A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed. We report that the ketyl radical produced by the single electron reduction of acyl azolium mediated by NHCs is a good coupling partner of alkenyl radicals, and the imidazole ions generated in this process directly activate alkylboronic acids to form alkyl radicals. This transformation mode is carried out under mild conditions and shows an excellent range of substrate applications.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3984-3989"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143766943","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
Carbene-catalyzed imine reductive reaction: a new application of Breslow intermediates† 碳催化亚胺还原反应：布雷斯洛中间体的新应用
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00332f
Hui Zhu , Han Xiao , Lihe Wang , Bo Jiang , Qingyun Wang , Shuquan Wu , Pengcheng Zheng
{"title":"Carbene-catalyzed imine reductive reaction: a new application of Breslow intermediates†","authors":"Hui Zhu ,&nbsp;Han Xiao ,&nbsp;Lihe Wang ,&nbsp;Bo Jiang ,&nbsp;Qingyun Wang ,&nbsp;Shuquan Wu ,&nbsp;Pengcheng Zheng","doi":"10.1039/d5qo00332f","DOIUrl":"10.1039/d5qo00332f","url":null,"abstract":"<div><div>α-Amino acids are vital structural motifs that are widely present in functional molecules. The catalytic hydrogenation and transfer hydrogenation of imines are significant methods for constructing α-amino acids. The general hydrogenation process often involves the use of numerous hazardous reagents. Here, we report a new NHC-catalyzed imine reductive reaction. The food additive acetoin is employed as a hydride source to react with the NHC catalyst, and a Breslow intermediate is then formed as a reductant to reduce the imino ester. The reaction can be further used to readily reduce various imine derivatives. Furthermore, the dengue virus inhibitor JNJ-A07 can be synthesized from the corresponding imino ester. Experimental and computational studies have been performed to disclose the reduction process. Our present study aims inspire a new avenue for the construction of α-amino acids <em>via</em> a mild and green reductive process.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3990-3997"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695857","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
C–H bond halogenation: unlocking regiodivergence and enhancing selectivity through directing group strategies 碳氢键卤化：通过定向基团策略解锁区域分化和提高选择性
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00372e
Palak Sharma , Vijay Luxami , Kamaldeep Paul
{"title":"C–H bond halogenation: unlocking regiodivergence and enhancing selectivity through directing group strategies","authors":"Palak Sharma ,&nbsp;Vijay Luxami ,&nbsp;Kamaldeep Paul","doi":"10.1039/d5qo00372e","DOIUrl":"10.1039/d5qo00372e","url":null,"abstract":"<div><div>Organohalides represent a crucial class of compounds widely used as key precursors for organometallic reagents, bioactive molecules, and nucleophilic substitution reactions. The increasing prominence of cross-coupling reactions has further elevated the importance of aryl halides, establishing them as key building blocks in organic synthesis. Recent advances in C–H functionalization have underscored the strategic role played by directing groups, in which functional groups act as internal ligands to facilitate C–H activation. This method has emerged as a highly efficient approach for forming C–C and C–X bonds with exceptional regioselectivity directly from otherwise inert C–H bonds. This review highlights recent progress in applying various functional groups, including carboxylic acids, aldehydes, amides, 8-aminoquinoline, <em>N</em>-oxides, PIP, pyridine, and other heterocyclic systems, as directing groups in C–H halogenation reactions over the past five years.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4066-4125"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144201548","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
Investigating the stereo-directing effect of remote participating groups on selectivity in the 2-deoxyglycosylation of galactal† 远距离参与基团对银河2-脱氧糖基化选择性的立体定向效应研究
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-11 DOI: 10.1039/d4qo02329c
Nitin Kumar , Ankit Yadav , Sudhir Kashyap
{"title":"Investigating the stereo-directing effect of remote participating groups on selectivity in the 2-deoxyglycosylation of galactal†","authors":"Nitin Kumar ,&nbsp;Ankit Yadav ,&nbsp;Sudhir Kashyap","doi":"10.1039/d4qo02329c","DOIUrl":"10.1039/d4qo02329c","url":null,"abstract":"<div><div>Chemical glycosylation is arguably crucial for assembling the structurally defined polysaccharides and glycoconjugates of distinctive biological functions. Predicting and governing the stereochemical outcome in the glycosylation reaction is undoubtedly more challenging and influenced mainly by the configuration of protecting groups (PGs) and ring conformers. In this paper, we exploited the direct influence of stereoelectronically diverse PGs on the anomeric selectivity in 2-deoxyglycosylation. The galactal donors with C-4 <em>O</em>-pivaloyl as a higher electron density group ensured enhanced α-selectivity; practically, trichloroacetimidate (<em>O</em>-TCA) ensured optimal selectivity, affirming the covalent remote group participation (RGP) featuring distinctive ring-bridging oxazepine structures. Mechanistic investigations employing density functional theory (DFT) and experimental studies revealed the perspective of RGP by distal C-4 PGs, which facilitate the stabilization of <sup><em>4</em></sup><em>H</em><sub><em>3</em></sub> and <sup><em>3</em></sup><em>H</em><sub><em>4</em></sub> conformations of oxocarbenium ions <em>via</em> dioxolenium species.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 11","pages":"Pages 3426-3437"},"PeriodicalIF":0.0,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570338","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
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