Tetrahedron chem最新文献_第9页

Hydrogen bond-mediated organocatalytic enantioselective reduction of nitroalkenes in deep eutectic solvents 深共晶溶剂中氢键介导的硝基烯烃的有机催化对映选择性还原

Tetrahedron chem Pub Date : 2023-06-01 DOI: 10.1016/j.tchem.2023.100038

Chiara Faverio, Monica Fiorenza Boselli, Tommaso Ruggiero, Laura Raimondi, Maurizio Benaglia

引用次数: 2

Catalysis by tertiary chalcogenonium salts 叔硫根铵盐的催化作用

Tetrahedron chem Pub Date : 2023-06-01 DOI: 10.1016/j.tchem.2023.100037

Ken Okuno, Ryuichi Nishiyori, Seiji Shirakawa

引用次数: 0

Evolution of design approaches in asymmetric organocatalysis over the last decade 过去十年不对称有机催化设计方法的演变

Tetrahedron chem Pub Date : 2023-03-01 DOI: 10.1016/j.tchem.2023.100035

Nika Melnyk , Marianne Rica Garcia , Iñigo Iribarren , Cristina Trujillo

引用次数: 1

A comprehensive study of tetracyanobutadiene push-pull chromophores derived from γ-pyranylidene γ-吡喃亚基四氰基丁二烯推挽发色团的综合研究

Tetrahedron chem Pub Date : 2023-03-01 DOI: 10.1016/j.tchem.2023.100036

Clotilde Philippe , Johann Melan , Alberto Barsella , Thomas Vives , Yann R. Leroux , Françoise Robin-Le Guen , Loïc Lemiègre , Denis Jacquemin , Sébastien Gauthier , Yann Trolez

{"title":"A comprehensive study of tetracyanobutadiene push-pull chromophores derived from γ-pyranylidene","authors":"Clotilde Philippe , Johann Melan , Alberto Barsella , Thomas Vives , Yann R. Leroux , Françoise Robin-Le Guen , Loïc Lemiègre , Denis Jacquemin , Sébastien Gauthier , Yann Trolez","doi":"10.1016/j.tchem.2023.100036","DOIUrl":"10.1016/j.tchem.2023.100036","url":null,"abstract":"<div><p>A new class of push-pull 1,1,4,4-tetracyanobutadienes (TCBDs) chromophores bearing a γ-pyranylidene as a pro-aromatic donor group have been developed, characterized and studied for their electrochemical, photophysical and second-order nonlinear optical (NLO) properties. [2 + 2] Cycloaddition-retroelectrocyclizations (CA-RE) with tetracyanoethylene (TCNE) allowed the formation of new TCBDs by taking advantage of the electron-donating ability of γ-pyranylidene functional groups. The limits of the reaction between TCNE and the corresponding alkynes have been investigated, both in terms of reactivity and solubility. Electrochemical studies of pyranylidene-TCBD <strong>1a-1j</strong> revealed two reversible reduction waves typical of TCBDs, and two oxidation waves originating from the γ-pyranylidene moiety. More complex electrochemical signals have been recorded when studying chromophores bearing multiple TCBD and/or γ-pyranylidene units. All pyranylidene-TCBDs showed panchromatic absorption properties, extending to the NIR in some cases. Changes made around the electron-withdrawing TCBD units significantly affected the ICT performance of the push-pull chromophores. Computational studies have been performed on this series of compounds to rationalize the origin of their optical properties. TD-DFT calculations confirmed that the synthesized pyranylidene-TCBDs are potential NLOphores. The second-order NLO properties of all chromophores were determined by the Electric Field-Induced Second Harmonic generation (EFISH) technique, and all systems exhibited valuable NLO properties with large <em>μβ</em><sub>EFISH</sub> values for purely organic compounds, up to 5700 10<sup>−48</sup> esu.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"5 ","pages":"Article 100036"},"PeriodicalIF":0.0,"publicationDate":"2023-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49236570","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: 3

Total synthesis of antiviral drug, nirmatrelvir (PF-07321332) 抗病毒药物nirmatrelvir (PF-07321332)的全合成

Tetrahedron chem Pub Date : 2022-12-01 DOI: 10.1016/j.tchem.2022.100033

Chandra Shekhar , Rajesh Nasam , Siva Ramakrishna Paipuri , Prakash Kumar , Kiranmai Nayani , Srihari Pabbaraja , Prathama S. Mainkar , Srivari Chandrasekhar

引用次数: 5

Synthesis, testing, and computational modeling of pleuromutilin 1,2,3-triazole derivatives in the ribosome 核糖体中胸膜残蛋白1,2,3-三唑衍生物的合成、测试和计算建模

Tetrahedron chem Pub Date : 2022-12-01 DOI: 10.1016/j.tchem.2022.100034

Logan M. Breiner , Anthony J. Briganti , Jennifer P. McCord , Moriah E. Heifetz , Sophia Y. Philbrook , Carla Slebodnick , Anne M. Brown , Andrew N. Lowell

{"title":"Synthesis, testing, and computational modeling of pleuromutilin 1,2,3-triazole derivatives in the ribosome","authors":"Logan M. Breiner , Anthony J. Briganti , Jennifer P. McCord , Moriah E. Heifetz , Sophia Y. Philbrook , Carla Slebodnick , Anne M. Brown , Andrew N. Lowell","doi":"10.1016/j.tchem.2022.100034","DOIUrl":"10.1016/j.tchem.2022.100034","url":null,"abstract":"<div><p>Pleuromutilin antimicrobials have given rise to the most recently FDA approved class of antibiotics for systemic human use. In this work, we describe a synthesis, assay, modeling approach to pleuromutilin development for the highly complex bacterial ribosome. Libraries of substituted 1,2,3-triazole derivatives were synthesized at the pleuromutilin C20 position by applying a recent anti-Markovnikov hydroazidation protocol to directly install an azido group, and at the C22 position through established methods. To learn about the interactions of these libraries with the ribosome and assess the potential for subsequent derivatization, an unbiased computational modeling method was used to biochemically rationalize binding modes of the C20 and C22 pleuromutilin derivatives. A pattern emerged where the triazole and its pendant chain, be it off the C20 or C22 position, moved to occupy the space vacated by the C22 sulfide group of clinical pleuromutilin compounds. Subsequent activity testing and comparative ranking of the computationally docked derivatives to the <em>in vitro</em> activity results showed a high predictability rating for the C22 substituted compounds. These combined investigations reveal potential restrictions and sites for expansion, paving the way for the development of future pleuromutilin derivates and other ribosome targeting antibiotics.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"4 ","pages":"Article 100034"},"PeriodicalIF":0.0,"publicationDate":"2022-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X22000304/pdfft?md5=e43345de0bd046dc559f5e89a9ec5f74&pid=1-s2.0-S2666951X22000304-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43717026","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: 1

Iodobenzene-catalyzed photochemical heteroarylation of alcohols by rupture of inert C–H and C–C bonds 通过破坏惰性碳氢键和碳碳键，碘苯催化醇的光化学异芳化反应

Tetrahedron chem Pub Date : 2022-12-01 DOI: 10.1016/j.tchem.2022.100031

Zhu Cao , Xinxin Wang , Xinxin Wu , Chen Zhu

引用次数: 0

Stereoconvergent, photocatalytic cyclopropanation reactions of β-substituted styrenes with ethyl diazoacetate β-取代苯乙烯与重氮乙酸乙酯的立体会聚光催化环丙化反应

Tetrahedron chem Pub Date : 2022-08-01 DOI: 10.1016/j.tchem.2022.100024

Tim Langletz, Claire Empel, Sripati Jana, Rene M. Koenigs

{"title":"Stereoconvergent, photocatalytic cyclopropanation reactions of β-substituted styrenes with ethyl diazoacetate","authors":"Tim Langletz, Claire Empel, Sripati Jana, Rene M. Koenigs","doi":"10.1016/j.tchem.2022.100024","DOIUrl":"10.1016/j.tchem.2022.100024","url":null,"abstract":"<div><p>Cyclopropanes constitute a pivotal molecular scaffold in medicinal and agrochemical research and find broad applications in marketed drugs and other bioactive compounds. Their synthesis commonly relies on metal-catalyzed carbene transfer reactions that necessitate the utilization of stereochemically defined olefin starting materials, which in turn requires a high stereochemical fidelity in the olefin synthesis step. Herein, we report on a photocatalytic strategy that allows the use of a mixture of the <em>E</em>- and <em>Z</em>-isomers of such olefins and gives access to a single isomer of the cyclopropane product in a stereoconvergent reaction. Experimental and theoretical data suggest the intermediacy of a triplet carbene intermediate that readily reacts with either isomer of the olefin. The intersystem crossing from triplet to singlet state proceeds in a diastereoselective fashion and can rationalize this stereoconvergent reaction. The application of this process was then examined with a diverse set of stereochemical mixtures of double- or triple-substituted olefins that readily undergo cyclopropanation disregarding of the stereochemical fidelity of the used olefin.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"3 ","pages":"Article 100024"},"PeriodicalIF":0.0,"publicationDate":"2022-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X22000201/pdfft?md5=77f34e961c576c5e05971eeca3fdae8e&pid=1-s2.0-S2666951X22000201-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42742698","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

Rhodium-catalyzed asymmetric hydroamination of gem-difluoroallenes with anilines 铑催化的宝石二氟烯与苯胺的不对称氢胺化反应

Tetrahedron chem Pub Date : 2022-08-01 DOI: 10.1016/j.tchem.2022.100023

Xiaowei Han, Yue Zhao, Zhuangzhi Shi , Minyan Wang

引用次数: 0

3,4-Dihydroquinoxalin-2-one privileged motif: A journey from classical chiral tools based synthesis to modern catalytic enantioselective strategies 3,4-二氢喹喔啉-2-酮特权基序：从经典手性工具合成到现代催化对映选择性策略

Tetrahedron chem Pub Date : 2022-08-01 DOI: 10.1016/j.tchem.2022.100027

Alessandra Lattanzi

{"title":"3,4-Dihydroquinoxalin-2-one privileged motif: A journey from classical chiral tools based synthesis to modern catalytic enantioselective strategies","authors":"Alessandra Lattanzi","doi":"10.1016/j.tchem.2022.100027","DOIUrl":"10.1016/j.tchem.2022.100027","url":null,"abstract":"<div><p>Optically pure 3,4-dihydroquinoxalin-2-ones, being members of the privileged quinoxaline family, received significant interest in organic synthesis, more particularly in medicinal chemistry, proving also to be useful building blocks for facile entry to a relevant bioactive pharmacophore, namely tetrahydroquinoxalines. The first asymmetric approaches to 3,4-dihydroquinoxalin-2-ones relied on classical use of chiral pool available reagents and auxiliares, such as α-amino acids and mandelates/tartaric acid derivatives, respectively. Over the years, more general and appealing enantioselective catalytic routes have been developed, mainly concerned with metal- and organocatalyzed reduction of quinoxalinones. Additionally, different organocatalytic cyclization strategies, including sustainable one-pot processes, have been added to the synthetic toolbox. This perspective aims to showcase the state of art of asymmetric approaches developed to prepare 3,4-dihydroquinoxalin-2-ones with a focus on catalytic routes, highlighting challenges and opportunities for future developments.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"3 ","pages":"Article 100027"},"PeriodicalIF":0.0,"publicationDate":"2022-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X22000237/pdfft?md5=1b6a973866b4c478d9d59867284ef28e&pid=1-s2.0-S2666951X22000237-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48708278","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