Tetrahedron chem最新文献

{"title":"Efficient construction of a quinoline framework from alcohols, nitroarenes, and alkenes promoted by a trimetallic catalyst system","authors":"Rikiya Horikawa ,&nbsp;Gen Onodera ,&nbsp;Tsutomu Fukuda ,&nbsp;Masanari Kimura","doi":"10.1016/j.tchem.2024.100108","DOIUrl":"10.1016/j.tchem.2024.100108","url":null,"abstract":"<div><div>A Pd/Fe/In-trimetallic catalyst system promotes the three-component coupling reaction of primary alcohols, nitroarenes, and terminal alkenes to construct quinoline frameworks in a single operation. These consecutive coupling reactions proceed via an oxidative Povarov reaction of alkenes and aldimines derived from primary alcohols and nitroarenes by a redox hydrogen transfer system. This reaction may contribute to the efficient development of pharmaceuticals and medicinal products.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100108"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592932","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}

{"title":"Erratum to “Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates” [Tetrahedron Chem 9 (2024) 100063]","authors":"Magdalena Piringer ,&nbsp;Lotte Stockhammer ,&nbsp;Lukas Vogl ,&nbsp;David Weinzierl ,&nbsp;Paul Zebrowski ,&nbsp;Mario Waser","doi":"10.1016/j.tchem.2024.100100","DOIUrl":"10.1016/j.tchem.2024.100100","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100100"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420379","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}

{"title":"Synthesis of allenones via nickel-catalyzed reductive coupling of propargyl esters with acyl chlorides","authors":"Zhen Song,&nbsp;Yueming Wang,&nbsp;Ming Ma,&nbsp;Yuanhong Ma","doi":"10.1016/j.tchem.2024.100113","DOIUrl":"10.1016/j.tchem.2024.100113","url":null,"abstract":"<div><div>Transition metal-catalyzed reductive coupling of two electrophilic components has proved to be a powerful and step-economic tool for forging diverse organic molecules. However, the application of such strategy for the synthesis of allenones that are very important in pharmaceutical chemistry and synthetic chemistry remains very limited and challenging. Herein, we have developed a nickel-catalyzed reductive cross-coupling of propargyl esters with acyl chlorides, which affords an alternative route for the synthesis of allenones. The current catalytic protocol features readily available starting materials, wide substrate scope, mild conditions and good regioselectivity.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100113"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129868","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}

{"title":"Betaketothioesters in organocatalysis: Harnessing nucleophilic reactivity, the fluorophobic effect, and expanding the substrate repertoire","authors":"Maciej Dajek ,&nbsp;Mikołaj J. Janicki ,&nbsp;Paulina D. Kubiak ,&nbsp;Julia Bąkowicz ,&nbsp;Błażej Dziuk ,&nbsp;Rafał Kowalczyk","doi":"10.1016/j.tchem.2024.100092","DOIUrl":"10.1016/j.tchem.2024.100092","url":null,"abstract":"<div><p>The use of thioesters as nucleophiles marks a considerable change in organic synthesis. This new method, propelled by gentle enolization with minimal catalyst loading, results in enantiomeric excesses surpassing 95 % under ambient conditions, accomplishing total conversion in merely 6 h. Remarkably, this method eliminates the need for additional functional groups in nitroalkenes for efficient chirality transfer from the organocatalyst. The exceptional reactivity of thioesters, combined with their water tolerance, enables reactions utilizing the hydrophobic effect, resulting in reaction times as short as 15 min and products with slightly enhanced stereoselectivity compared to analogous reactions in dichloromethane. Additionally, reactions performed in perfluorinated solvents outpace their homogenous counterparts in organic solvents, delivering products in shorter time with comparable stereoselectivity. This work highlights the rare utilization of the fluorous effect in organocatalysis. Simple squaramides also exhibit remarkable catalytic activity in the reactions of beta-keto thioesters with alpha-bromo nitroalkenes. As little as 0.1 mol% of the catalyst leads to product formation with an 86 % yield (qNMR) and 93 % enantiomeric excess. Upscaling the reaction does not significantly affect the enantiomeric excess but leads to a slight decrease in yield from 82 % to 77 %. It has been demonstrated that thioesters react more rapidly than their ketoester counterparts, and the two-step reaction leading to dihydrofuran ring closure is entirely accomplished by extending the reaction time, eliminating the need for additional base. The examples presented here expand the range of substrates derived from carboxylic acid esters in catalytic reactions, suggesting the potential for the synthesis of challenging reactions in analogs of alkoxyl esters. Additional KS-DFT calculations shed more light on the reaction paths, rationalizing the observed stereochemical outcomes.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100092"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000317/pdfft?md5=e8c77ccd308b186191ed4d3a27f7cdfd&pid=1-s2.0-S2666951X24000317-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142241038","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}

{"title":"(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst","authors":"Samuel Redl,&nbsp;Christoph Topf","doi":"10.1016/j.tchem.2024.100089","DOIUrl":"10.1016/j.tchem.2024.100089","url":null,"abstract":"<div><p>We communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates and alkynes. The introduced protocol is free from any ex ante modifications of the used Cu(I) precursors by air-sensitive phosphines or elaborate <em>N</em>-heterocyclic carbene ligands. The conjugate hydrogenation of enoates and the (selective) reduction of C<img>C bonds is achieved through a [Cu(CH₃CN)₄]⁺/<em>tert</em>-butoxide pair whereby we describe a delicate influence of the base cation on the chemoselectivity of the respective transformation. In case of the ester-to-alcohol reduction, a combination of simple CuI and NaO<em>t</em>Bu proved to be successful. Deuteration experiments are included to address certain mechanistic aspects of the introduced catalytic system. All requisite chemicals are readily obtainable through commercial channels and the catalyst assembly is set up on the bench without the need for special lab-technical precautions.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100089"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000287/pdfft?md5=5437e19b8968da8070a19157b748e4dc&pid=1-s2.0-S2666951X24000287-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142151336","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}

{"title":"Recent trends in the identification and engineering of halogenases","authors":"Huibin Wang ,&nbsp;Ikuro Abe","doi":"10.1016/j.tchem.2024.100112","DOIUrl":"10.1016/j.tchem.2024.100112","url":null,"abstract":"<div><div>Halogenation significantly enhances the biological activity, stability, and solubility of organic molecules, and thus is a crucial modification in the biotechnology and pharmaceutical industries. Halogenases, the core enzymes responsible for this transformation, are invaluable tools for the selective incorporation of halogens into diverse substrates, offering vast potential in drug development and synthetic biology. Recent discoveries of novel classes of halogenases have substantially expanded the repertoire of enzymatic halogenation. In parallel, remarkable progress in the protein engineering of halogenases is leading to unprecedented opportunities in the synthesis of novel compounds. These efforts have not only expanded the substrate scope, improved the selectivity, and enhanced the catalytic activity but also demonstrated their capacity for new-to-nature reactions. This perspective article highlights critical developments in the identification and engineering of halogenases, underscoring their growing significance in biocatalysis and sustainable chemical production. Continued exploration of novel halogenases, coupled with advanced protein engineering strategies, will open new frontiers in biocatalyst development and drug discovery.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100112"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705642","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}

{"title":"Electrochemical dibromoacetoxylation and trihalogenation of allylarenes","authors":"Yong Jiang ,&nbsp;Fumei Ke ,&nbsp;Chen Zhu ,&nbsp;Daixi Li ,&nbsp;Tao Shen","doi":"10.1016/j.tchem.2024.100106","DOIUrl":"10.1016/j.tchem.2024.100106","url":null,"abstract":"<div><div>Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of C<img>C bond and oxidative functionalization of benzylic C–H bond.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100106"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142560584","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}

{"title":"Tyrosine bioconjugation using stably preparable urazole radicals","authors":"Shinichi Sato ,&nbsp;Shogo Miyano ,&nbsp;Keita Nakane ,&nbsp;Zhengyi Liu ,&nbsp;Munehiro Kumashiro ,&nbsp;Tomohide Saio ,&nbsp;Yuya Tanaka ,&nbsp;Akira Shigenaga ,&nbsp;Chizu Fujimura ,&nbsp;Eri Koyanagi ,&nbsp;Hafumi Nishi ,&nbsp;Shusuke Tomoshige ,&nbsp;Minoru Ishikawa","doi":"10.1016/j.tchem.2024.100111","DOIUrl":"10.1016/j.tchem.2024.100111","url":null,"abstract":"<div><div>Our <em>ex situ</em> tyrosine bioconjugation method utilizes the oxidation of <em>N</em>-methylurazole by Bobbitt's salt or electrochemical activation to generate stable radicals for selective tyrosine labeling, thereby addressing the longstanding challenges in protein bioconjugation. Unlike traditional tyrosine conjugation techniques that rely on closed-shell chemistry with 1,2,4-triazoline-3,5-dione derivatives, this method introduces an alternative bond-forming mechanism that expands bioconjugation through a radical-based pathway that enhances tyrosine selectivity. The applicability of this method was demonstrated for various proteins and validated through proteome-wide analyses, highlighting its potential as a valuable tool for investigating protein function and interaction dynamics.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100111"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705643","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}

{"title":"Erratum to “Latest updates in ElectroPhotoChemical reactions” [Tetrahedron Chem 9 (2024) 100061]","authors":"F. Medici,&nbsp;V. Chiroli,&nbsp;L. Raimondi,&nbsp;M. Benaglia","doi":"10.1016/j.tchem.2024.100099","DOIUrl":"10.1016/j.tchem.2024.100099","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100099"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420380","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}

{"title":"Erratum to “Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements” [Tetrahedron Chem 1 (2022) 100007]","authors":"Jing-Yi Wang ,&nbsp;Shuming Zhang ,&nbsp;Xian-Yang Yu ,&nbsp;Yu-Hao Wang ,&nbsp;Hong-Lin Wan ,&nbsp;Shu Zhang ,&nbsp;Wei Tan ,&nbsp;Feng Shi","doi":"10.1016/j.tchem.2024.100096","DOIUrl":"10.1016/j.tchem.2024.100096","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100096"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420381","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}