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Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone 三肽催化的 β-硝基苯炔与环己酮的不对称迈克尔加成反应
Synlett Pub Date : 2024-04-15 DOI: 10.1055/a-2307-0645
Kippei Maeda, Mitsuki Takeyama, Yoshihito Kohari, Miki Murata
{"title":"Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone","authors":"Kippei Maeda, Mitsuki Takeyama, Yoshihito Kohari, Miki Murata","doi":"10.1055/a-2307-0645","DOIUrl":"https://doi.org/10.1055/a-2307-0645","url":null,"abstract":"A tripeptide catalyst derived from natural L-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-Fluoro-4-ChloroBenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0℃ for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92%ee).","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"42 43","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140701601","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
Efficient Synthesis of Difluoroacrylamide/Amine From Fluorinated Olefins Under Base Promotion 在碱促进下从氟化烯烃高效合成二氟丙烯酰胺/胺
Synlett Pub Date : 2024-04-15 DOI: 10.1055/a-2307-0567
Yang Li, Y. Shi, Zhi Bo Li, Hong Li, W. Zhu, Q. Fan, Xin Yue Li
{"title":"Efficient Synthesis of Difluoroacrylamide/Amine From Fluorinated Olefins Under Base Promotion","authors":"Yang Li, Y. Shi, Zhi Bo Li, Hong Li, W. Zhu, Q. Fan, Xin Yue Li","doi":"10.1055/a-2307-0567","DOIUrl":"https://doi.org/10.1055/a-2307-0567","url":null,"abstract":"Difluoroacrylamides/amines are an important class of fluorinated compounds. Here, we report an efficient synthesis method for difluoroacrylamides without the use of transition metals. Under simple base promoted conditions, 3-bromo-3,3-difluoroprop-1-ene can react with aniline or mono-substituted aniline, removing one molecule of HBr to obtain the target compound. The substituent can be methyl or acryloyl. Another efficient method for synthesizing difluoroalkenes is the reaction of 2-bromo-3,3,3-trifluoroprop-1-ene with indole, which can also yield difluoroalkenes under standard conditions.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"281 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140704090","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
Improved Synthesis of Pseudoproline and DMB Dipeptide Carboxylic Acids 改进伪脯氨酸和 DMB 二肽羧酸的合成
Synlett Pub Date : 2024-04-15 DOI: 10.1055/a-2306-9316
Wyatt C. Powell, Kelly Johnson, Peyton Tran, Ruiheng Jing, Maciej Walczak
{"title":"Improved Synthesis of Pseudoproline and DMB Dipeptide Carboxylic Acids","authors":"Wyatt C. Powell, Kelly Johnson, Peyton Tran, Ruiheng Jing, Maciej Walczak","doi":"10.1055/a-2306-9316","DOIUrl":"https://doi.org/10.1055/a-2306-9316","url":null,"abstract":"We report a mild method for the preparation of Fmoc-protected dipeptides containing a DMB (HMB) group or modified as pseudoprolines. To minimize the loss of the Fmoc protection, we optimized the saponification conditions and included a calcium additive that protected the other base-sensitive functionalities and improved the yield of the free acid (36-82%). The reaction requires a combination of CaCl2 and NaOH in a mixture of i-PrOH and water at room temperature.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"23 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140702009","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
Iron catalyzed oxidative Csp3-Csp3 radical coupling reaction between thiohydantoins and O-acetyl oximes for the synthesis of 1,3-dibenzyl-3,4-dihydropyrrolo[2,3-d]imidazole-2(1H)-thione derivatives 铁催化硫代海因和 O-乙酰肟之间的 Csp3-Csp3 氧化自由基偶联反应，用于合成 1,3- 二苄基-3,4-二氢吡咯并[2,3-d]咪唑-2(1H)-硫酮衍生物
Synlett Pub Date : 2024-04-09 DOI: 10.1055/a-2302-0450
P. P. Patel, K. Chikhalia
{"title":"Iron catalyzed oxidative Csp3-Csp3 radical coupling reaction between thiohydantoins and O-acetyl oximes for the synthesis of 1,3-dibenzyl-3,4-dihydropyrrolo[2,3-d]imidazole-2(1H)-thione derivatives","authors":"P. P. Patel, K. Chikhalia","doi":"10.1055/a-2302-0450","DOIUrl":"https://doi.org/10.1055/a-2302-0450","url":null,"abstract":"A unified heteroannelation method to achieve the synthesis of 1,3-dibenzyl-3,4-dihydropyrrolo[2,3-d]imidazole-2(1H)-thione derivatives with an iron catalyst is proposed. The annelation reaction is followed by Csp3-Csp3 radical coupling between thiohydantoins and O-acetyl oximes. The synthetic approach enables access to several alkynylated thiohydantoins and O-acetyl oximes with controlled selectivity for Csp3-Csp3 coupling rather than Csp3-O coupling in moderate to higher yield. The optimization study has been carried out by changing catalyst loading, oxidants, solvents, and varying temperatures. Synthesized compounds were characterized through 1H NMR, 13C NMR, and mass spectral studies.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"2 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140727826","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 Improved Iodine-Catalyzed Aromatization Reaction and Its Application in the Synthesis of a Key Intermediate of Cannabidiol 改进的碘催化芳香化反应及其在合成大麻二酚关键中间体中的应用
Synlett Pub Date : 2024-04-09 DOI: 10.1055/a-2301-2431
Safomuddin Abduahadi, Emmanuel Mintah Bonku, Hongjian Qin, Abdullajon Odilov, F. Zhu, H. Aisa, Jingshan Shen
{"title":"An Improved Iodine-Catalyzed Aromatization Reaction and Its Application in the Synthesis of a Key Intermediate of Cannabidiol","authors":"Safomuddin Abduahadi, Emmanuel Mintah Bonku, Hongjian Qin, Abdullajon Odilov, F. Zhu, H. Aisa, Jingshan Shen","doi":"10.1055/a-2301-2431","DOIUrl":"https://doi.org/10.1055/a-2301-2431","url":null,"abstract":"In this study, the development of an improved process for the synthesis of a key cannabidiol intermediate, methyl olivetolate, is described. The process involves an improvement of the iodine-catalyzed aromatization of cyclohexanone using potassium persulfate as an oxidant. This approach enabled for the efficient synthesis of methyl olivetolate with a 90% yield and 99.84% HPLC purity on a 5 kg scale. Additionally, a total of 16 cyclohexanone substrates afforded higher yields (75-92%) of m-diphenol compounds compared to the established methods.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"20 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140722544","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
Brønsted Acid-Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans 布氏酸催化的烯丙基醇分子内烯丙基取代反应：2-乙烯基色氨酸的简便合成
Synlett Pub Date : 2024-04-08 DOI: 10.1055/a-2301-9223
Yun-Fan Li, Yu-Ting Xi, Kai-Ji Hu, Q. Tan, Chang-Hua Ding, Bin Xu
{"title":"Brønsted Acid-Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans","authors":"Yun-Fan Li, Yu-Ting Xi, Kai-Ji Hu, Q. Tan, Chang-Hua Ding, Bin Xu","doi":"10.1055/a-2301-9223","DOIUrl":"https://doi.org/10.1055/a-2301-9223","url":null,"abstract":"Brønsted acid-catalyzed intramolecular allylic substitution reaction of secondary and tertiary allylic alcohols has been developed. A variety of 2-vinylchromans were efficiently prepared in moderate to excellent yields. The given method features wide substrate scope, operational simplicity, metal-free, and mild reaction conditions. The practicability of the method was demonstrated by the gram-scale reaction and further derivations of the product. Catalytic asymmetric reaction was preliminarily studied.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"33 21","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140732104","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
Phenylazo-BODIPYs: Direct Access via Pd-Catalysis 苯基偶氮-BODIPYs：通过 Pd 催化直接获取
Synlett Pub Date : 2024-04-06 DOI: 10.1055/a-2301-2854
Sebastian H Röttger, Anjuli Birk, Burkhard Butschke, Peter G. Jones, D. Werz
{"title":"Phenylazo-BODIPYs: Direct Access via Pd-Catalysis","authors":"Sebastian H Röttger, Anjuli Birk, Burkhard Butschke, Peter G. Jones, D. Werz","doi":"10.1055/a-2301-2854","DOIUrl":"https://doi.org/10.1055/a-2301-2854","url":null,"abstract":"A new type of functionalized BODIPY dyes is described. Utilizing an established procedure for Buchwald-Hartwig reactions, we have been able to convert -chloro BODIPYs to α-azo-BODIPYs using phenylhydrazines. Optimization of the reaction conditions and variation of the BODIPY core and the phenylhydrazine were conducted. Absorption and emission spectra were recorded.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"39 19","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140734209","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
Advances in the Synthesis of S-containing Cyclic Architectures via Insertion of SO2 通过插入二氧化硫合成含 S 环结构的研究进展
Synlett Pub Date : 2024-04-06 DOI: 10.1055/a-2301-2909
Xi Lu, Yuyang Huang, Yuxing Yang, Chao Shu
{"title":"Advances in the Synthesis of S-containing Cyclic Architectures via Insertion of SO2","authors":"Xi Lu, Yuyang Huang, Yuxing Yang, Chao Shu","doi":"10.1055/a-2301-2909","DOIUrl":"https://doi.org/10.1055/a-2301-2909","url":null,"abstract":"Sulfur-containing heterocycles, where the S(R) moiety is in the cyclic structures, have been found tremendous applications in the field of chemistry, pharmaceutical, and materials sciences due to the unique chemical, biological and pharmaceutical activities. The recent years have witnessed an increasing interest in sulfur-containing heterocycles preparation and new methods were reported with modern methodologies and technologies through insertion of sulfur dioxide. The main objective of this mini-review is to overview the latest major developments for the synthesis of sulfur-containing heterocycles systems, mainly covering thermoinduced cyclization, photoinduced cyclization and electroninduced cyclization through the insertion of SO2. We wish to bring readers a comprehensive understanding and provide a positive outlook for the promising future of this field.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"39 21","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140734084","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
Introduction of the N-amino group into 4-(tetrazol-5-yl)-5-nitro-1,2,3-triazole: a strategy for enhancing density and performance of energetic materials 在 4-(四唑-5-基)-5-硝基-1,2,3-三唑中引入 N-氨基：提高高能材料密度和性能的策略
Synlett Pub Date : 2024-04-02 DOI: 10.1055/a-2298-0282
Huang Xun, Zhao Pinxu, Hai-feng Huang, Jun Yang
{"title":"Introduction of the N-amino group into 4-(tetrazol-5-yl)-5-nitro-1,2,3-triazole: a strategy for enhancing density and performance of energetic materials","authors":"Huang Xun, Zhao Pinxu, Hai-feng Huang, Jun Yang","doi":"10.1055/a-2298-0282","DOIUrl":"https://doi.org/10.1055/a-2298-0282","url":null,"abstract":"2-Amino-5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (4, HANTT), its energetic salts 5-7 and the azo compound 8 were successfully synthesized. Compared to 5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (H2NTT), the neutral N-amino compound HANTT exhibits excellent properties in many aspects, such as higher density (ρ = 1.86 g cm–3), better detonation performance (Dv = 8931 m s–1, P = 32.2 GPa) and higher thermal decomposition temperature (Td = 237 oC). Among them, the hydroxylammonium salt 6 exhibited the best detonation performance (Dv = 9096 m s–1, P = 32.8 GPa) and the acceptable mechanical sensitivity (IS = 12 J, FS = 144 N). All these compounds 4-8 were fully characterized by infrared spectroscopy, multinuclear NMR spectroscopies, elemental analysis and differential scanning calorimetry.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"246 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140751166","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
Erratum: Solvent Effect on Base-Free Synthesis 4-Substituted 2-Oxazolines via Intramolecular Cyclodemesylation 批注：通过分子内环二甲基化无碱合成 4-取代的 2-恶唑啉的溶剂效应
Synlett Pub Date : 2024-04-01 DOI: 10.1055/s-0043-1774863
Erdin Dalkılıç, Yakup Güneş
{"title":"Erratum: Solvent Effect on Base-Free Synthesis 4-Substituted 2-Oxazolines via Intramolecular Cyclodemesylation","authors":"Erdin Dalkılıç, Yakup Güneş","doi":"10.1055/s-0043-1774863","DOIUrl":"https://doi.org/10.1055/s-0043-1774863","url":null,"abstract":"","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"74 24","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140769681","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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