Pub Date : 2024-11-08DOI: 10.1016/j.tetlet.2024.155360
Sergey V. Karpov, Yakov S. Kaukov, Alexey V. Eremkin, Oleg E. Nasakin
Under the conditions of a modified “one-pot” Zincke reaction, novel aza-merocyanines based on the dimer of malononitrile, pyridine, and α-iodonicotinonitrile derivatives were synthesized. It was demonstrated that in the presence of weak bases, the solutions of the obtained compounds exhibit fluorescence with λmaxem around 660 nm, accompanied by a color change from pale yellow to violet. Interaction of these aza-merocyanines with the potassium salt of the malononitrile dimer yielded a new glutaconaldehyde derivative, which can be used for the quantitative fluorimetric determination of Fe3+ ions at low concentrations.
{"title":"Zincke reaction in the synthesis of novel glutaconaldehyde derivatives: Synthesis of potassium 2,10-diamino-1,1,3,9,11,11-hexacyanoundeca-2,4,6,8,10-pentaen-1-ide and its application for fluorimetric quantitative determination of Fe3+ ions","authors":"Sergey V. Karpov, Yakov S. Kaukov, Alexey V. Eremkin, Oleg E. Nasakin","doi":"10.1016/j.tetlet.2024.155360","DOIUrl":"10.1016/j.tetlet.2024.155360","url":null,"abstract":"<div><div>Under the conditions of a modified “one-pot” Zincke reaction, novel aza-merocyanines based on the dimer of malononitrile, pyridine, and α-iodonicotinonitrile derivatives were synthesized. It was demonstrated that in the presence of weak bases, the solutions of the obtained compounds exhibit fluorescence with λ<sub>max</sub><sup>em</sup> around 660 nm, accompanied by a color change from pale yellow to violet. Interaction of these aza-merocyanines with the potassium salt of the malononitrile dimer yielded a new glutaconaldehyde derivative, which can be used for the quantitative fluorimetric determination of Fe<sup>3+</sup> ions at low concentrations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155360"},"PeriodicalIF":1.5,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662324","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed via the reaction of carbon disulfide with N-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with in situ prepared dithiocarbamic acid. The products were obtained in good to high yields.
{"title":"Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines","authors":"Azim Ziyaei Halimehjani , Farzaneh Noorakhtar , Zahra Marjani","doi":"10.1016/j.tetlet.2024.155361","DOIUrl":"10.1016/j.tetlet.2024.155361","url":null,"abstract":"<div><div>An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed <em>via</em> the reaction of carbon disulfide with <em>N</em>-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with <em>in situ</em> prepared dithiocarbamic acid. The products were obtained in good to high yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155361"},"PeriodicalIF":1.5,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-06DOI: 10.1016/j.tetlet.2024.155339
Km Garima , Vishal Srivastava , Praveen P. Singh , Pravin K. Singh
An effective and advantageous one-pot multicomponent photo-induced methodology has been developed for the synthesis of biologically potent 2-amino-4H-1,3-oxa/thiazine from substituted benzaldehyde, ethynylbenzene and urea/thiourea catalyzed by eosin-Y at room temperature using EtOH as a green solvent with wide range of applications in pharmaceutical and agriculture industries. This proposed work emphasizes to investigate an accessible, safe, easy and convenient method for the synthesis of 2-amino oxa/thiazine derivatives with good to excellent yield.
{"title":"One-pot multicomponent photo-induced eosin-Y catalyzed synthesis of 2-amino oxa/thiazine derivatives","authors":"Km Garima , Vishal Srivastava , Praveen P. Singh , Pravin K. Singh","doi":"10.1016/j.tetlet.2024.155339","DOIUrl":"10.1016/j.tetlet.2024.155339","url":null,"abstract":"<div><div>An effective and advantageous one-pot multicomponent photo-induced methodology has been developed for the synthesis of biologically potent 2-amino-4<em>H</em>-1,3-oxa/thiazine from substituted benzaldehyde, ethynylbenzene and urea/thiourea catalyzed by eosin-Y at room temperature using EtOH as a green solvent with wide range of applications in pharmaceutical and agriculture industries. This proposed work emphasizes to investigate an accessible, safe, easy and convenient method for the synthesis of 2-amino oxa/thiazine derivatives with good to excellent yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155339"},"PeriodicalIF":1.5,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592695","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-05DOI: 10.1016/j.tetlet.2024.155355
Wei Zhang, Guohao Wu, Ying Wang, Yanhua Zhang
A continuous flow reactor packed with glass fiber-supported palladium nanoparticles (PdNPs/GF) is designed and successfully applied in the controllable hydrogenation of arylacetylenes with sodium borohydride (NaBH4) in methanol. By adjusting the flow rate, the substrate concentration and the amount of NaBH4, the selectivity of the products are tunable as desired. It is interesting that fully hydrogenated products (aryl alkanes) are obtained with up to 95 % yield at a flow rate of 1.5 mL/min with a substrate concentration of 5.0 mM and 3.0 eq. of NaBH4. On the other hand, the selective semi-hydrogenation transformation is much easier to achieve, and the yield of aryl olefins is up to 87 %. This fixed-bed system offers a simple and efficient method for the hydrogenation of arylacetylenes, which has great potential in the future scale-up syntheses.
{"title":"Controllable hydrogenation of arylacetylenes with NaBH4 catalyzed by palladium nanoparticles in a fixed-bed system","authors":"Wei Zhang, Guohao Wu, Ying Wang, Yanhua Zhang","doi":"10.1016/j.tetlet.2024.155355","DOIUrl":"10.1016/j.tetlet.2024.155355","url":null,"abstract":"<div><div>A continuous flow reactor packed with glass fiber-supported palladium nanoparticles (PdNPs/GF) is designed and successfully applied in the controllable hydrogenation of arylacetylenes with sodium borohydride (NaBH<sub>4</sub>) in methanol. By adjusting the flow rate, the substrate concentration and the amount of NaBH<sub>4</sub>, the selectivity of the products are tunable as desired. It is interesting that fully hydrogenated products (aryl alkanes) are obtained with up to 95 % yield at a flow rate of 1.5 mL/min with a substrate concentration of 5.0 mM and 3.0 eq. of NaBH<sub>4</sub>. On the other hand, the selective semi-hydrogenation transformation is much easier to achieve, and the yield of aryl olefins is up to 87 %. This fixed-bed system offers a simple and efficient method for the hydrogenation of arylacetylenes, which has great potential in the future scale-up syntheses.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155355"},"PeriodicalIF":1.5,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586185","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.
一氧化碳（CO）荧光探针因其检测限低、特异性强、操作简单和良好的生物相容性而备受关注。然而，针对不同的应用，分子结构与荧光响应信号之间的关系仍有待系统阐明。本文设计并合成了基于萘二甲酰亚胺衍生物的三种不同的 CO 荧光探针，它们分别具有蓝色发射（B-NIA）、绿色发射（G-NIA）和近红外发射（R-NIA）。通过调节荧光团的共轭体系和荧光识别基团的位置，实现了对 CO 的三基色和相反的开启或关闭荧光响应。通过理论计算和质谱分析，研究了荧光响应的变化和检测 CO 的传感机制。所有 B/G/R-NIA 都具有较高的 CO 检测灵敏度。值得注意的是，R-NIA 对 CO 具有明显的近红外荧光响应，检测限低（0.61 µM），且具有高选择性和相对 pH 稳定性。此外，R-NIA 的细胞毒性特别低，已成功用于检测活细胞中的 CO。这些研究为合成不同发射波长、对一氧化碳具有相反荧光响应的荧光探针提供了理论参考和技术路线，可用于各种应用场景。
{"title":"Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response","authors":"Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao","doi":"10.1016/j.tetlet.2024.155357","DOIUrl":"10.1016/j.tetlet.2024.155357","url":null,"abstract":"<div><div>Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155357"},"PeriodicalIF":1.5,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586186","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-02DOI: 10.1016/j.tetlet.2024.155358
Vladimir D. Fedorenko, Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
2-Arylideneindan-1,3-diones readily undergo [3+2]-cycloaddition with N-methylazomethine ylide derived from sarcosine and formaldehyde to give 4′-aryl-1′-methylspiro[indene-2,3′-pyrrolidine]-1,3-diones, which were further cyclized in perchloric acid to (3aR*,7bR*,12aR*)-7b-hydroxy-2-methyl-2,3,3a,7b-tetrahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrrol-12(1H)-ones in 33–100 % yields.
{"title":"Diastereoselective synthesis of novel alkaloid-like 1,2,3,3a,7b,12-hexahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrroles","authors":"Vladimir D. Fedorenko, Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh","doi":"10.1016/j.tetlet.2024.155358","DOIUrl":"10.1016/j.tetlet.2024.155358","url":null,"abstract":"<div><div>2-Arylideneindan-1,3-diones readily undergo [3+2]-cycloaddition with <em>N</em>-methylazomethine ylide derived from sarcosine and formaldehyde to give 4′-aryl-1′-methylspiro[indene-2,3′-pyrrolidine]-1,3-diones, which were further cyclized in perchloric acid to (3a<em>R*</em>,7b<em>R*</em>,12a<em>R*</em>)-7b-hydroxy-2-methyl-2,3,3a,7b-tetrahydroindeno[2′,1′:2,3]indeno[1,2-<em>c</em>]pyrrol-12(1<em>H</em>)-ones in 33–100 % yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155358"},"PeriodicalIF":1.5,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662321","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The mechanism of the nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides is investigated using density functional theory calculations. The calculation result shows that the reaction mechanism involves sequential steps of C–F bond oxidative addition, decarbonylation, alkyl radical addition, C(sp2)–C(sp3) reductive elimination to afford the product, single electron transfer (SET) and reduction by Zn to regenerate the initiating complex. And the step of C–F bond oxidative addition was found to be the rate-determining step. The decarbonylation should occur before the alkyl radical addition. The effects of 1,3-bis(diphenylphosphino)propane (DPPP) ligand and different substrates on the reactivity were also analyzed. These calculation results disclosed the detailed reaction mechanism and shed lights on some ambiguous suggestions from experiments.
{"title":"DFT study on mechanism of nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides","authors":"Lijuan Liu, Zhenfeng Shang, Ruifang Li, Xiufang Xu","doi":"10.1016/j.tetlet.2024.155353","DOIUrl":"10.1016/j.tetlet.2024.155353","url":null,"abstract":"<div><div>The mechanism of the nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides is investigated using density functional theory calculations. The calculation result shows that the reaction mechanism involves sequential steps of C–F bond oxidative addition, decarbonylation, alkyl radical addition, C(sp<sup>2</sup>)–C(sp<sup>3</sup>) reductive elimination to afford the product, single electron transfer (SET) and reduction by Zn to regenerate the initiating complex. And the step of C–F bond oxidative addition was found to be the rate-determining step. The decarbonylation should occur before the alkyl radical addition. The effects of 1,3-bis(diphenylphosphino)propane (DPPP) ligand and different substrates on the reactivity were also analyzed. These calculation results disclosed the detailed reaction mechanism and shed lights on some ambiguous suggestions from experiments.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155353"},"PeriodicalIF":1.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662318","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-30DOI: 10.1016/j.tetlet.2024.155348
Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev
A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH4Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.
{"title":"An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides","authors":"Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev","doi":"10.1016/j.tetlet.2024.155348","DOIUrl":"10.1016/j.tetlet.2024.155348","url":null,"abstract":"<div><div>A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH<sub>4</sub>Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155348"},"PeriodicalIF":1.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662320","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-28DOI: 10.1016/j.tetlet.2024.155338
Jeonghwan Park , Sujin Lee , Young Taek Han
Irrepairzepine (1), a unique benzoazepinoquinolinone alkaloid isolated from an endophytic fungus, exhibits synthetic lethality targeting in PTEN-deficient glioblastoma cells. Herein, the first synthesis of irrepairzepine was achieved through a series of high-yielding reactions. The key steps include the synthesis of quinoline via the Au(I)-catalyzed cycloisomerization of N-propargyl aniline and construction of the azepinone core through the acid-catalyzed lactamization of an aminophenyl cyanoquinoline precursor, which was prepared using a simple umpolung approach that involves regioselective bromination followed by the Rosenmund-von Braun reaction.
从一种内生真菌中分离出的一种独特的苯并氮杂卓喹啉酮生物碱--伊瑞西平（IRREPZEPINE）(1)，在缺乏 PTEN 的胶质母细胞瘤细胞中表现出合成致死性。在此，我们通过一系列高产反应首次合成了伊瑞西平。关键步骤包括通过 Au(I)-catalyzed cycloisomerization of N-propargyl aniline（N-丙炔基苯胺的 Au(I)-catalyzed cycloisomerization）合成喹啉，以及通过酸催化氨基苯基氰基喹啉前体的内酰胺化来构建氮杂环庚酮核心。
{"title":"Total synthesis of natural benzoazepinoquinolinone alkaloid irrepairzepine via Au(I)-catalyzed cycloisomerization and regioselective functionalization","authors":"Jeonghwan Park , Sujin Lee , Young Taek Han","doi":"10.1016/j.tetlet.2024.155338","DOIUrl":"10.1016/j.tetlet.2024.155338","url":null,"abstract":"<div><div>Irrepairzepine (<strong>1</strong>), a unique benzoazepinoquinolinone alkaloid isolated from an endophytic fungus, exhibits synthetic lethality targeting in PTEN-deficient glioblastoma cells. Herein, the first synthesis of irrepairzepine was achieved through a series of high-yielding reactions. The key steps include the synthesis of quinoline via the Au(I)-catalyzed cycloisomerization of <em>N</em>-propargyl aniline and construction of the azepinone core through the acid-catalyzed lactamization of an aminophenyl cyanoquinoline precursor, which was prepared using a simple umpolung approach that involves regioselective bromination followed by the Rosenmund-von Braun reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155338"},"PeriodicalIF":1.5,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-28DOI: 10.1016/j.tetlet.2024.155347
Yinuo Xiao, Zhenpeng Li, Changming Xu
A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.
我们开发了一种手性螺环季铵盐催化的不对称烷基化（尤其是甲基化）α-芳基酯的方法，这种酯在强碱性条件下固有的反应性很差，但却能得到高达 94 % ee 的目标产物。这种温和的工艺还被用于合成光学纯萘普生。
{"title":"Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates","authors":"Yinuo Xiao, Zhenpeng Li, Changming Xu","doi":"10.1016/j.tetlet.2024.155347","DOIUrl":"10.1016/j.tetlet.2024.155347","url":null,"abstract":"<div><div>A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155347"},"PeriodicalIF":1.5,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142552888","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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