Tetrahedron chem最新文献

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Erratum to “Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions” [Tetrahedron Chem 11 (2024) 100086] 对 "基本条件下涉及元素硫活化的有机反应的活性和机理 "的勘误 [Tetrahedron Chem 11 (2024) 100086]
Tetrahedron chem Pub Date : 2024-10-05 DOI: 10.1016/j.tchem.2024.100102
Peter Conen , Michael A.R. Meier
{"title":"Erratum to “Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions” [Tetrahedron Chem 11 (2024) 100086]","authors":"Peter Conen , Michael A.R. Meier","doi":"10.1016/j.tchem.2024.100102","DOIUrl":"10.1016/j.tchem.2024.100102","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100102"},"PeriodicalIF":0.0,"publicationDate":"2024-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420266","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
Erratum to “Hydrogen bond-mediated organocatalytic enantioselective reduction of nitroalkenes in deep eutectic solvents” [Tetrahedron Chem 6 (2023) 100038] 对 "氢键介导的有机催化对映选择性还原深共晶溶剂中的硝基烯 "的勘误 [Tetrahedron Chem 6 (2023) 100038]
Tetrahedron chem Pub Date : 2024-10-05 DOI: 10.1016/j.tchem.2024.100097
Chiara Faverio, Monica Fiorenza Boselli, Tommaso Ruggiero, Laura Raimondi, Maurizio Benaglia
{"title":"Erratum to “Hydrogen bond-mediated organocatalytic enantioselective reduction of nitroalkenes in deep eutectic solvents” [Tetrahedron Chem 6 (2023) 100038]","authors":"Chiara Faverio, Monica Fiorenza Boselli, Tommaso Ruggiero, Laura Raimondi, Maurizio Benaglia","doi":"10.1016/j.tchem.2024.100097","DOIUrl":"10.1016/j.tchem.2024.100097","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100097"},"PeriodicalIF":0.0,"publicationDate":"2024-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420382","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
Erratum to “Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates” [Tetrahedron Chem 9 (2024) 100063] 对 "催化生成的 C1-刘易斯碱烯醇的对映体选择性 α-杂官能化反应 "的勘误 [Tetrahedron Chem 9 (2024) 100063]
Tetrahedron chem Pub Date : 2024-10-04 DOI: 10.1016/j.tchem.2024.100100
Magdalena Piringer , Lotte Stockhammer , Lukas Vogl , David Weinzierl , Paul Zebrowski , Mario Waser
{"title":"Erratum to “Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates” [Tetrahedron Chem 9 (2024) 100063]","authors":"Magdalena Piringer , Lotte Stockhammer , Lukas Vogl , David Weinzierl , Paul Zebrowski , 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":"2024-10-04","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}
引用次数: 0
Erratum to “Latest updates in ElectroPhotoChemical reactions” [Tetrahedron Chem 9 (2024) 100061] 对 "电光化学反应的最新进展 "的勘误 [Tetrahedron Chem 9 (2024) 100061]
Tetrahedron chem Pub Date : 2024-10-04 DOI: 10.1016/j.tchem.2024.100099
F. Medici, V. Chiroli, L. Raimondi, M. Benaglia
{"title":"Erratum to “Latest updates in ElectroPhotoChemical reactions” [Tetrahedron Chem 9 (2024) 100061]","authors":"F. Medici, V. Chiroli, L. Raimondi, 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":"2024-10-04","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}
引用次数: 0
Erratum to “Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements” [Tetrahedron Chem 1 (2022) 100007] 有机催化不对称合成具有生物活性的六氢吡咯并[2,3-b]吲哚-含多手性元素的四取代烯烃》勘误 [Tetrahedron Chem 1 (2022) 100007]
Tetrahedron chem Pub Date : 2024-10-04 DOI: 10.1016/j.tchem.2024.100096
Jing-Yi Wang , Shuming Zhang , Xian-Yang Yu , Yu-Hao Wang , Hong-Lin Wan , Shu Zhang , Wei Tan , Feng Shi
{"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 , Shuming Zhang , Xian-Yang Yu , Yu-Hao Wang , Hong-Lin Wan , Shu Zhang , Wei Tan , 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":"2024-10-04","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}
引用次数: 0
Synthesis of spiro[4.4]nonane-containing functional organic molecules 合成含螺[4.4]壬烷的功能有机分子
Tetrahedron chem Pub Date : 2024-09-26 DOI: 10.1016/j.tchem.2024.100095
Zhuo Wang , Chunngai Hui , Hu Wang
{"title":"Synthesis of spiro[4.4]nonane-containing functional organic molecules","authors":"Zhuo Wang ,&nbsp;Chunngai Hui ,&nbsp;Hu Wang","doi":"10.1016/j.tchem.2024.100095","DOIUrl":"10.1016/j.tchem.2024.100095","url":null,"abstract":"<div><div>Spiro[4.4]nonane features are an important scaffold in many applications such as enantioenriched ligands, functional materials, natural products, and polymers. Excited by the prospect of the spiro[4.4]nonane scaffold, its structural intricacy still appears challenging in chemical synthesis. Many functional organic molecules possessing spiro[4.4]nonane scaffold(s) have recently been reported and synthesized. We provide a <em>Minireview</em> highlighting such advancements and discuss the future opportunities of spiro[4.4]nonane scaffolds in organic chemistry. Representative examples from 2019 to 2024 are discussed.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100095"},"PeriodicalIF":0.0,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142420265","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
Betaketothioesters in organocatalysis: Harnessing nucleophilic reactivity, the fluorophobic effect, and expanding the substrate repertoire 有机催化中的硫代叔丁酯:利用亲核反应性、疏氟效应和扩大底物范围
Tetrahedron chem Pub Date : 2024-09-10 DOI: 10.1016/j.tchem.2024.100092
Maciej Dajek , Mikołaj J. Janicki , Paulina D. Kubiak , Julia Bąkowicz , Błażej Dziuk , Rafał Kowalczyk
{"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":"2024-09-10","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}
引用次数: 0
Palladium-catalyzed desymmetric coupling reaction between silacyclobutanes and terminal alkynes for the synthesis of silicon-stereogenic allyl vinylsilanes 钯催化硅环丁烷与末端炔烃的不对称偶联反应,用于合成硅稳定烯丙基乙烯基硅烷
Tetrahedron chem Pub Date : 2024-09-07 DOI: 10.1016/j.tchem.2024.100093
Zhi-Yuan Chen , Zi-Lu Wang , Jin-Bo Zhao , Yun-He Xu
{"title":"Palladium-catalyzed desymmetric coupling reaction between silacyclobutanes and terminal alkynes for the synthesis of silicon-stereogenic allyl vinylsilanes","authors":"Zhi-Yuan Chen ,&nbsp;Zi-Lu Wang ,&nbsp;Jin-Bo Zhao ,&nbsp;Yun-He Xu","doi":"10.1016/j.tchem.2024.100093","DOIUrl":"10.1016/j.tchem.2024.100093","url":null,"abstract":"<div><div>A palladium/TADDOL-derived phosphonate catalyzed desymmetric ring-opening coupling bewteen prochiral silacyclobutanes and alkyl terminal alkynes was developed. This catalytic system facilitates the formation of optically active allyl vinylsilane compounds featuring a quaternary silicon-stereogenic center, achieving good to high yields and moderate to good enantiomeric ratios. This approach significantly broaden the scope of ring-opening desymmetrization reactions involving silacyclobutanes under transition metal catalysis.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100093"},"PeriodicalIF":0.0,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000329/pdfft?md5=073e3035c3d6920f145a27af2ba1c7ee&pid=1-s2.0-S2666951X24000329-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142314789","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
Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization 双(18-冠-6)-1,3-二苯乙烯通过氢键自组装和[2 + 2]光环加成:2.2]metacyclophanes 的立体选择性合成和蝶式热异构化
Tetrahedron chem Pub Date : 2024-08-18 DOI: 10.1016/j.tchem.2024.100091
Timofey P. Martyanov , Artem P. Vorozhtsov , Evgeny N. Ushakov , Nikita A. Slesarenko , Ilia V. Sulimenkov , Sergey P. Gromov
{"title":"Self-assembly via hydrogen bonding of bis(18-crown-6)-1,3-distyrylbenzene and [2 + 2] photocycloaddition: Stereoselective synthesis of [2.2]metacyclophanes and butterfly-type thermal isomerization","authors":"Timofey P. Martyanov ,&nbsp;Artem P. Vorozhtsov ,&nbsp;Evgeny N. Ushakov ,&nbsp;Nikita A. Slesarenko ,&nbsp;Ilia V. Sulimenkov ,&nbsp;Sergey P. Gromov","doi":"10.1016/j.tchem.2024.100091","DOIUrl":"10.1016/j.tchem.2024.100091","url":null,"abstract":"<div><p>The photochemistry of bis(18-crown-6)-containing 1,3-distyrylbenzene and its 2 : 2 bis-pseudo-sandwich complex with ethane-1,2-diammonium was studied. The UV irradiation of the supramolecular complex resulted in the formation of three geometric isomers of tetracrown-containing dicyclobutano[2.2]metacyclopane, differing in the orientation of the cyclobutane moieties, with the unsymmetrical isomer (&gt;50 %) predominating. The diammonium cations used as the template could be removed after photolysis by simple extraction, and the product was obtained in high yield (82 %). The <sup>1</sup>H NMR signals of a mixture of geometric isomers of [2.2]metacyclophane derivative were assigned resorting to quantum chemistry methods (DFT). The kinetic and thermodynamic parameters of thermal isomerization between the <em>endo</em>,<em>endo</em>- and <em>exo</em>,<em>exo</em>-isomers were measured. Tetracrown-containing dicyclobutano[2.2]metacyclophanes are homotetratopic ligands that contain four binding sites for metal and ammonium cations, which is of interest for the design of photo- and thermo-switchable supramolecular devices with a variable complex formation behavior and supramolecular machines owing to the butterfly-type thermal isomerization.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100091"},"PeriodicalIF":0.0,"publicationDate":"2024-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000305/pdfft?md5=bbc61009297f58bea762604b4ff7acfe&pid=1-s2.0-S2666951X24000305-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142098210","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
(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst (利用多功能微粒铜催化剂对烯酸盐和炔烃进行(半)氢化反应
Tetrahedron chem Pub Date : 2024-08-15 DOI: 10.1016/j.tchem.2024.100089
Samuel Redl, Christoph Topf
{"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(CH<sub>3</sub>CN)<sub>4</sub>]<sup>+</sup>/<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":"2024-08-15","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}
引用次数: 0
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