Tetrahedron chem最新文献

{"title":"Pd(II)-catalyzed C–H annulation and lactonization of indole-2-carboxamides with hydroxyalkynoates using air as an oxidant","authors":"Kiran Aswale ,&nbsp;Rajashaker Bantu ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tchem.2024.100104","DOIUrl":"10.1016/j.tchem.2024.100104","url":null,"abstract":"<div><div>A novel palladium(II) catalyzed C–H annulation strategy has been developed for the synthesis of a diverse range of furo[3′,4':5,6]pyrido[3,4-<em>b</em>]indole-1,5(3<em>H</em>)-dione scaffolds. This is the first report on the construction of polycyclic carboline frameworks from indole-2-carboxamides and 4-hydroxy-2-alkynoates. This method provides a direct access to fused carbolines that are closely resemble to biologically active <em>β</em>-carboline frameworks.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100104"},"PeriodicalIF":0.0,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578720","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 “Palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated sp3 C–H bonds” [Tetrahedron Chem 7 (2023) 100046]","authors":"Robbie Ge ,&nbsp;Faith Herington ,&nbsp;Alana Mangawang ,&nbsp;Debabrata Maiti ,&nbsp;Haibo Ge","doi":"10.1016/j.tchem.2024.100098","DOIUrl":"10.1016/j.tchem.2024.100098","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100098"},"PeriodicalIF":0.0,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142416417","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 “Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions” [Tetrahedron Chem 11 (2024) 100086]","authors":"Peter Conen ,&nbsp;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}

{"title":"Erratum to “Hydrogen bond-mediated organocatalytic enantioselective reduction of nitroalkenes in deep eutectic solvents” [Tetrahedron Chem 6 (2023) 100038]","authors":"Chiara Faverio,&nbsp;Monica Fiorenza Boselli,&nbsp;Tommaso Ruggiero,&nbsp;Laura Raimondi,&nbsp;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}

{"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":"2024-10-04","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}

{"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":"2024-10-04","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}

{"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":"2024-10-04","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}

{"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}

{"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}

{"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}