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Total Synthesis of Moiramide B Using an Allylic Alkylation Approach 使用烯丙基烷基化方法全合成莫伊酰胺 B
IF 2 4区 化学
Synlett Pub Date : 2024-04-02 DOI: 10.1055/s-0042-1751578
{"title":"Total Synthesis of Moiramide B Using an Allylic Alkylation Approach","authors":"","doi":"10.1055/s-0042-1751578","DOIUrl":"https://doi.org/10.1055/s-0042-1751578","url":null,"abstract":"An allylic side chain is introduced onto a chiral γ-amino-β-ketoamide by a Pd-catalyzed allylic alkylation. Subsequent ozonolysis and oxidation proceed only with Cbz-protected ketoamides. The total synthesis of moiramide B is finalized by peptide coupling.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"38 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560600","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}
引用次数: 0
Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes 不对称 1,1-二芳基烯的立体选择性合成
IF 2 4区 化学
Synlett Pub Date : 2024-04-02 DOI: 10.1055/s-0042-1751580
{"title":"Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes","authors":"","doi":"10.1055/s-0042-1751580","DOIUrl":"https://doi.org/10.1055/s-0042-1751580","url":null,"abstract":"1,1-Diborylalkene, a class of important diboryl species, serves as the synthetic precursor of multisubstituted olefin, which is a prevalent building block in natural products, functional materials, and pharmaceuticals. Current methods mainly afford symmetrical 1,1-diborylalkenes, and late-stage differentiation of the two identical boryl groups is required to achieve selective difunctionalization. In comparison, stereoselective synthesis of unsymmetrical 1,1-diborylalkenes (UDBA) are less-explored. This Synpacts article provides a brief summary of the achievements in the synthesis of UDBAs. In particularly, we highlight our recent work on the unsymmetrical 1,1-diborylation of alkynes using a neutral sp2–sp3 diboron reagent to access UDBAs and their controllable stepwise derivatization.1 Introduction2 Background: Unsymmetrical 1,1-Diborylalkene Synthesis3 Stereoselective Unsymmetrical 1,1-Diborylation of Alkynes with a Neutral sp2–sp3 Diboron Reagent4 Summary and Outlook","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"5 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560515","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}
引用次数: 0
TfOH-Catalyzed Facile Access for One-Pot Synthesis of β-Acylamino Ketones by Avoiding the Usage of Acetyl Chloride 避免使用乙酰氯，在 TfOH 催化下轻松实现 β-酰氨基酮的一锅合成
IF 2 4区 化学
Synlett Pub Date : 2024-03-28 DOI: 10.1055/s-0042-1751579
Sachin D. Kharat, Prasad B. Rupnavar, Keshav S. Pakhare, Ayesha A. Khan, Bapurao D. Rupanawar, Mahadev P. Shinde
{"title":"TfOH-Catalyzed Facile Access for One-Pot Synthesis of β-Acylamino Ketones by Avoiding the Usage of Acetyl Chloride","authors":"Sachin D. Kharat, Prasad B. Rupnavar, Keshav S. Pakhare, Ayesha A. Khan, Bapurao D. Rupanawar, Mahadev P. Shinde","doi":"10.1055/s-0042-1751579","DOIUrl":"https://doi.org/10.1055/s-0042-1751579","url":null,"abstract":"<p>We have developed a TfOH-catalyzed, highly efficient protocol for the synthesis of biologically active β-acylamino ketones from aldehyde, ketone, and nitrile by avoiding the use of acetyl chloride. The reaction proceeds through a sequential aldol reaction followed by a nucleophilic attack of nitrile and hydrolysis of nitrile in one pot. The attractive features of this tandem process are mild reaction conditions, high atom economy, broad substrate scope with 51–87% yield, gram-scale reaction, and ease of operation.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"6 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140324592","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}
引用次数: 0
Electrochemical Efficient Synthesis of Two Azo Energetic Compounds 电化学高效合成两种偶氮能化合物
IF 2 4区 化学
Synlett Pub Date : 2024-03-27 DOI: 10.1055/a-2283-5829
Jinhao Zhang, Yulan Song, Wenjia Hao, Rufang Peng, Bo Jin
{"title":"Electrochemical Efficient Synthesis of Two Azo Energetic Compounds","authors":"Jinhao Zhang, Yulan Song, Wenjia Hao, Rufang Peng, Bo Jin","doi":"10.1055/a-2283-5829","DOIUrl":"https://doi.org/10.1055/a-2283-5829","url":null,"abstract":"<p>Azo compounds with a high density, high enthalpy, and excellent detonation performance have received increasing research attention. The conventional method of chemical dehydrogenation that is used to form azo compounds involves the use of strong oxidants, resulting in environmental pollution. Electrochemical organic synthesis is considered an old method and a new technology. In this work, azofurazan tetrazole {H<sub>2</sub>AzFT; 5,5′-[diazene-1,2-diylbis(1,2,5-oxadiazole-4,3-diyl)]bis-1<i>H</i>-tetrazole} and azofurazan hydroxytetrazole (H<sub>2</sub>AzFTO) were synthesized by a green and efficient electrochemical dehydrogenation coupling of 5-(4-aminofurazan-3-yl)-1<i>H</i>-tetrazole and 5-(4-aminofurazan-3-yl)-1-hydroxytetrazole, respectively. The structures of H<sub>2</sub>AzFT and (NH<sub>4</sub>)<sub>2</sub>AzFTO were fully characterized by infrared spectroscopy, nuclear magnetic resonance, and elemental analysis, and their thermal stabilities were determined by differential thermal analysis.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"14 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140315911","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}
引用次数: 0
Late-Stage C–H Deuteration of Organic Compounds via Ligand-Enabled Palladium-Catalyzed Hydrogen Isotope Exchange 通过配体催化的钯催化氢同位素交换实现有机化合物的后期 C-H Deuteration
IF 2 4区 化学
Synlett Pub Date : 2024-03-22 DOI: 10.1055/s-0042-1751566
Jyotirmoy Dey, Manuel van Gemmeren
{"title":"Late-Stage C–H Deuteration of Organic Compounds via Ligand-Enabled Palladium-Catalyzed Hydrogen Isotope Exchange","authors":"Jyotirmoy Dey, Manuel van Gemmeren","doi":"10.1055/s-0042-1751566","DOIUrl":"https://doi.org/10.1055/s-0042-1751566","url":null,"abstract":"<p>Over the past years our lab has established a research program towards the late-stage introduction of deuterium into organic molecules using Pd-catalyzed reversible C–H activation as a means to affect hydrogen isotope exchange. Through catalyst design, including the introduction of novel ligand scaffolds, as well as the use of strategically chosen optimization and screening approaches, e.g., exploiting microscopic reversibility by first optimizing de-deuteration processes or using a multi-substrate screening approach, our studies have resulted in a number of synthetically useful labelling protocols and are described herein from a personal perspective.</p> <p>1 Introduction</p> <p>2 β-C(sp<sup>3</sup>)–H Deuteration of Free Carboxylic Acids</p> <p>3 Nondirected C–H Deuteration of Arenes</p> <p>4 Nondirected C–H Deuteration of Heteroarenes</p> <p>5 Conclusion</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"30 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199231","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}
引用次数: 0
The Difunctionalization of Alkenes Completed by DMTSM and CF3SO2Na without Metal Catalysts DMTSM 和 CF3SO2Na 在不使用金属催化剂的情况下完成的烯烃双官能化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-22 DOI: 10.1055/a-2283-5928
Siwei Shen, Jinzhao Gao, Xiaofeng Luo, Tianqiang Wang, Peihua Liu, Rulong Yan
{"title":"The Difunctionalization of Alkenes Completed by DMTSM and CF3SO2Na without Metal Catalysts","authors":"Siwei Shen, Jinzhao Gao, Xiaofeng Luo, Tianqiang Wang, Peihua Liu, Rulong Yan","doi":"10.1055/a-2283-5928","DOIUrl":"https://doi.org/10.1055/a-2283-5928","url":null,"abstract":"<p>The electrophilic thiolation of alkenes initiated by DMTSM and the addition of CF<sub>3</sub>SO<sub>2</sub>Na in one pot has been developed. This reaction also can be extended to ArSO<sub>2</sub>Na. This protocol features a good substrate scope, simple procedures, and mild reaction conditions and affords the desired products in moderate yields without metal catalysts.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"144 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199030","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}
引用次数: 0
A Simple Tool to Benchmark Reactivity in Asymmetric Catalysis 不对称催化反应基准的简单工具
IF 2 4区 化学
Synlett Pub Date : 2024-03-21 DOI: 10.1055/s-0042-1751576
Alberto Muñoz, Tomislav Rovis
{"title":"A Simple Tool to Benchmark Reactivity in Asymmetric Catalysis","authors":"Alberto Muñoz, Tomislav Rovis","doi":"10.1055/s-0042-1751576","DOIUrl":"https://doi.org/10.1055/s-0042-1751576","url":null,"abstract":"<p>Herein, we report a simple and noninvasive experimental protocol in which a series of relative reaction rates may be obtained by way of single competition experiments. This approach permits a quantitative comparison of any given number of chiral catalysts relative to a ‘benchmarking’ chiral catalyst – a particularly useful tool since catalyst design and selection have remained largely dependent on chemical intuition. We apply this benchmarking approach towards an asymmetric <i>N</i>-heterocyclic carbene (NHC) catalyzed intramolecular Stetter reaction as a proof-of-concept study. In doing so, we demonstrate a rapid method to assess the complex interplay between catalyst reactivity and stereoelectronic effects – an analytical approach that has heretofore not been attempted for NHCs. To showcase the generality of this method, we apply it to an enantioselective Rh(I)-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and aryl alkynes for a series of chiral phosphoramidite ligands. The results described herein demonstrate that this inexpensive and easily adoptable protocol can reveal complex yet subtle steric and stereoelectronic effects of vastly different chiral catalyst structures, which can further aid with catalyst development and selection for a clearly defined application.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"144 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199211","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}
引用次数: 0
Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids 铑催化的 2-(1H-吲哚-1-羰基)苯甲酸分子内脱羰基芳基化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-20 DOI: 10.1055/a-2278-5797
Hirotsugu Suzuki, Yosuke Takemura, Takanori Matsuda
{"title":"Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids","authors":"Hirotsugu Suzuki, Yosuke Takemura, Takanori Matsuda","doi":"10.1055/a-2278-5797","DOIUrl":"https://doi.org/10.1055/a-2278-5797","url":null,"abstract":"<p>We developed a redox-neutral synthesis of isoindoloindolone via intramolecular arylation of 2-(1<i>H</i>-indole-1-carbonyl)benzoic acids. This protocol facilitates the formation of various substituted isoindoloindolones in yields ranging from 17% to 80%. Our mechanistic investigations indicate the pivotal role of NaI: the iodide anion promotes the formation of the desired isoindoloindolone, and the sodium cation suppresses the formation of acylated byproducts, thereby enabling the selective formation of isoindoloindolones in acceptable yields.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"1 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199176","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}
引用次数: 0
The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes 未活化烯烃的电化学反式氯甲酰氧基化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-20 DOI: 10.1055/s-0043-1763695
Jona Queder, Gerhard Hilt
{"title":"The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes","authors":"Jona Queder, Gerhard Hilt","doi":"10.1055/s-0043-1763695","DOIUrl":"https://doi.org/10.1055/s-0043-1763695","url":null,"abstract":"<p>An attempted aryl selenium-catalyzed formation of <i>cis</i>-chlorohydrins from alkenes was unsuccessful but led to an electrochemical investigation for the <i>trans</i>-selective chloroformyloxylation of cyclic and acyclic alkenes in moderate to good yields. Interestingly, when 1,1-disubstituted alkenes were used, the corresponding vinyl chloride derivatives were obtained, and the application of 1-phenylcyclohex-1-ene led to the formation of an allyl chloride derivative.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"102 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199224","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}
引用次数: 0
Bioorthogonal Chemistry at Radboud University: Past, Present and Future 拉德布德大学的生物正交化学：过去、现在和未来
IF 2 4区 化学
Synlett Pub Date : 2024-03-14 DOI: 10.1055/s-0042-1751569
Floris P. J. T. Rutjes, Kimberly M. Bonger, Kevin Neumann
{"title":"Bioorthogonal Chemistry at Radboud University: Past, Present and Future","authors":"Floris P. J. T. Rutjes, Kimberly M. Bonger, Kevin Neumann","doi":"10.1055/s-0042-1751569","DOIUrl":"https://doi.org/10.1055/s-0042-1751569","url":null,"abstract":"<p>Over the past two decades, bioorthogonal chemistry has profoundly impacted various chemistry-related fields, including chemical biology and drug delivery. This transformative progress stems from collaborative efforts involving chemists and biologists, underscoring the importance of interdisciplinary research. In this Account, we present the developments in bioorthogonal chemistry within our Institute for Molecules and Materials at Radboud University. The chemistry disclosed here spans from strained alkynes and alkenes to drug release and bioconjugation strategies, mirroring the extensive scope provided by bioorthogonal chemistry. By reflecting on the chemistry originating at Radboud University, this Account emphasizes that teamwork is essential for driving significant progress in bioorthogonal chemistry.</p> <p>1 Introduction</p> <p>2 Providing BCN as a Robust Bioorthogonal Tool for Chemical Biology and Beyond</p> <p>3 Towards Readily Available Click-to-Release <i>trans</i>-Cyclooctenes</p> <p>4 Giving Molecules Guidance</p> <p>5 Next Generation of Bioconjugation Strategies: Dynamic Click Chemistry</p> <p>6 Conclusions</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"57 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140152795","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}
引用次数: 0
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