Tetrahedron chem最新文献_第7页

Latest updates in ElectroPhotoChemical reactions 电光化学反应的最新进展

Tetrahedron chem Pub Date : 2023-12-25 DOI: 10.1016/j.tchem.2023.100061

F. Medici , V. Chiroli, L. Raimondi , M. Benaglia

{"title":"Latest updates in ElectroPhotoChemical reactions","authors":"F. Medici , V. Chiroli, L. Raimondi , M. Benaglia","doi":"10.1016/j.tchem.2023.100061","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100061","url":null,"abstract":"<div><p>In the last twenty years, electrochemistry and photochemistry have attracted a renewed and still uprising interest in organic synthesis. Two of the most simple and abundant reagents, electrons and photons, became the key players in synthetic chemistry as cornerstones of developing greener and sustainable chemical processes. An interesting strategy that recently emerged is the possibility of merging the two worlds in what is called ElectroPhotoChemistry (EPC). In particular, this review will focus on the most recent contributions in the field. The basic principles of EPC will be presented along with a discussion of the published works of the last few years. Electrophotochemical oxidation/reduction reactions will be discussed, including in this section the transformations of a C–H bond to a C-X (X: heteroatom). In the C–H activation chapter the formation of C–C bond, starting from a C–H bond, will be considered. Finally, the miscellaneous chapter includes examples which do not clearly belong to the previous categories.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"9 ","pages":"Article 100061"},"PeriodicalIF":0.0,"publicationDate":"2023-12-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X2300027X/pdfft?md5=39901c65a1a77116384777ef9d4b7040&pid=1-s2.0-S2666951X2300027X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139099781","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

Strategic use of crude H2 for the catalytic reduction of carbonyl compounds 将粗 H2 用于羰基化合物催化还原的战略用途

Tetrahedron chem Pub Date : 2023-12-23 DOI: 10.1016/j.tchem.2023.100059

Mahiro Sakuraba , Sensuke Ogoshi , Yoichi Hoshimoto

引用次数: 0

Biomimetic synthetic studies on the hicksoane alkaloids 山核桃烷生物碱的仿生合成研究

Tetrahedron chem Pub Date : 2023-12-19 DOI: 10.1016/j.tchem.2023.100060

Stephanie Lee, Tilo Söhnel, Jonathan Sperry

引用次数: 0

Total synthesis of 1,2,11,12E-tetradehydrohardwickiic acid 1,2,11,12E-四氢哈德猕猴酸的全合成

Tetrahedron chem Pub Date : 2023-12-09 DOI: 10.1016/j.tchem.2023.100057

Wenming Zhu , Duo Zhang , Yucheng Li, Ming Yang

{"title":"Total synthesis of 1,2,11,12E-tetradehydrohardwickiic acid","authors":"Wenming Zhu , Duo Zhang , Yucheng Li, Ming Yang","doi":"10.1016/j.tchem.2023.100057","DOIUrl":"10.1016/j.tchem.2023.100057","url":null,"abstract":"<div><p>Clerodane diterpenoids are a large class of natural products found in various species and exhibit a wide range of biological activities. <em>trans</em>-Clerodanes, which feature a <em>trans</em>-decalin core structure, are the most common subfamily of clerodane diterpenoids. Previously, we have developed a tail-to-head cyclization strategy <em>via</em> a titanium(III) catalyzed alkyne terminated radical polyene cyclization to synthesis C18 non-oxidized <em>trans</em>-clerodanes and sesquiterpene (hydro)quinones with a similar <em>trans</em>-decalin skeleton. In this communication, we reported the first asymmetric total synthesis of 1,2,11,12<em>E</em>-tetradehydrohardwickiic acid, a C18 oxidized <em>trans</em>-clerodane, through the product of titanium(III) catalyzed tail-to-head polyene cyclization of the derivative of farnesol. A hydroxyl group directed hydrogenation of alkene, an <em>E</em>-selective hydrobromination of terminal alkyne, and a Suzuki coupling were the key steps of the synthesis.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"9 ","pages":"Article 100057"},"PeriodicalIF":0.0,"publicationDate":"2023-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X23000232/pdfft?md5=4dc335a6b0a5b36ae7d33b8add32eafa&pid=1-s2.0-S2666951X23000232-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138621513","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

Multiple Isocyanide insertions promoted by protic and Lewis acids 原酸和路易斯酸促进多种异氰酸酯插入

Tetrahedron chem Pub Date : 2023-12-09 DOI: 10.1016/j.tchem.2023.100056

John Kornfeind, Fraser F. Fleming

{"title":"Multiple Isocyanide insertions promoted by protic and Lewis acids","authors":"John Kornfeind, Fraser F. Fleming","doi":"10.1016/j.tchem.2023.100056","DOIUrl":"10.1016/j.tchem.2023.100056","url":null,"abstract":"<div><p>The protonation, or Lewis Acid complexation, of electrophiles can trigger the sequential insertion of two or more isocyanides resulting in valuable iminonitriles or heterocycles. The number of insertions is controlled by the nature of the alkyl- or arylisocyanide and by the presence of a proximal nucleophile capable of attacking the intermediate nitrilium; loss of an alkyl group from the nitrilium or attack by a nucleophile terminates further isocyanide insertions. The mechanistic survey of protic and Lewis acid-promoted isocyanide insertions aims to provide a fundamental understanding of the reactivity and selectivity to facilitate synthetic applications. The review is structured with an introductory overview followed by a mechanistic analysis before moving to a survey of double insertions, which are the most prevalent, then triple insertions; the survey concludes with the sole example of a quadruple insertion. The hope is that the insight contained in the review will aid in applying protic and Lewis acid-activated isocyanide insertions to prepare an array of complex heterocycles.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"9 ","pages":"Article 100056"},"PeriodicalIF":0.0,"publicationDate":"2023-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X23000220/pdfft?md5=20f0f51e5e580d9f8eb947e27e3285d6&pid=1-s2.0-S2666951X23000220-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138615244","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

Recent developments in transition metal-catalyzed asymmetric borrowing hydrogen catalysis 过渡金属催化的不对称借氢催化研究进展

Tetrahedron chem Pub Date : 2023-12-01 DOI: 10.1016/j.tchem.2023.100054

Nidhi Garg, Ishika Agrawal, Dhananjay Satav, Doppalapudi Vineet Kumar, Basker Sundararaju

{"title":"Recent developments in transition metal-catalyzed asymmetric borrowing hydrogen catalysis","authors":"Nidhi Garg, Ishika Agrawal, Dhananjay Satav, Doppalapudi Vineet Kumar, Basker Sundararaju","doi":"10.1016/j.tchem.2023.100054","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100054","url":null,"abstract":"<div><p>Asymmetric Borrowing Hydrogen (BH) catalysis is a versatile, one-step approach for synthesizing enantioenriched amines/carbonyl derivatives from biomass-derived oxidized hydrocarbons with water as the sole by-product. These valuable chiral moieties are ubiquitous in natural products, fragrances, agrochemicals, and pharmaceuticals; hence, efficient methodologies that can directly form C–C and C–N bonds to diversify the synthetic utility are highly desired. Over the last decade, numerous contributions involving noble metals have been documented in this area, which largely relies on the choice of a suitable transition metal catalyst that facilitates a succession of oxidation/reduction steps. Only very recently, 3d metals were utilized for C–C and C–N bond formation in an asymmetric manner using the BH strategy. This article describes the current state-of-the-art for controlling the stereochemistry in the formation of a new stereogenic center <em>via</em> multiple catalysis, rational ligand design, <em>etc</em>. Several other strategies are outlined, such as asymmetric reductive functionalization, dynamic kinetic resolution, enantioconvergent processes, <em>etc</em>. New chiral catalysts based on 3d metals are anticipated to arise and find applications in the field of asymmetric borrowing hydrogen catalysis.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100054"},"PeriodicalIF":0.0,"publicationDate":"2023-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X23000207/pdfft?md5=c87883cd936f5a5efe186b0f8c5a6c25&pid=1-s2.0-S2666951X23000207-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138471694","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

The visible-light-promoted intermolecular para-cycloadditions of allenamides on naphthalene 可见光促进烯丙酰胺在萘上的分子间对环加成

Tetrahedron chem Pub Date : 2023-11-10 DOI: 10.1016/j.tchem.2023.100053

Maurizio Chiminelli, Gabriele Scarica, Davide Balestri, Luciano Marchiò, Nicola Della Ca’, Giovanni Maestri

引用次数: 0

Catalytic, dearomative 2,3-difluorination of indoles 吲哚催化脱芳2,3-二氟化反应

Tetrahedron chem Pub Date : 2023-11-08 DOI: 10.1016/j.tchem.2023.100052

Fang-Hai Tu , Shuang Lin , Ya-Jie Tang , Li-Cai Liu , Qingjiang Li , Honggen Wang

{"title":"Catalytic, dearomative 2,3-difluorination of indoles","authors":"Fang-Hai Tu , Shuang Lin , Ya-Jie Tang , Li-Cai Liu , Qingjiang Li , Honggen Wang","doi":"10.1016/j.tchem.2023.100052","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100052","url":null,"abstract":"<div><p>Indolines, characterized by their diverse biological activities and structural significance, have garnered considerable attention in the realms of natural product synthesis and drug discovery. Concurrently, the incorporation of fluorine atoms into organic molecules has emerged as a powerful strategy to enhance their pharmacological properties. Herein, we report a robust and diastereoselective approach for the synthesis of 2,3-difluorinated indolines through the iodine(I/III)-catalyzed dearomatization of readily available indoles. The protocol operates under mild conditions, displaying excellent functional group tolerance and remarkable diastereoselectivity. By employing this developed protocol, vicinal-difluorinated analogues of indole-containing drugs can be efficiently accessed. Theoretical calculations have shed light on the underlying reaction mechanism, proposing the formation of a β-fluorine-substituted carbocation intermediate. It is postulated that the observed high diastereoselectivity can be attributed to the dipole-dipole interactions facilitated by the C–F bond. Crystallographic analysis has revealed the profound impact of fluorine atom introduction on the conformational preferences of the indoline core. Given the unique structural characteristics and pharmacological significance of 2,3-difluorinated indolines, we anticipate their widespread application in medicinal chemistry and drug discovery endeavors.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100052"},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X23000189/pdfft?md5=70151845dd1856e460c59fa1eee21990&pid=1-s2.0-S2666951X23000189-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134656522","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

Synthesis and application of stimulus-triggered cyclic caged oligonucleotides for gene expression regulation 刺激触发环笼寡核苷酸的合成及其在基因表达调控中的应用

Tetrahedron chem Pub Date : 2023-10-24 DOI: 10.1016/j.tchem.2023.100051

Wen-Da Chen , Liang Cheng

{"title":"Synthesis and application of stimulus-triggered cyclic caged oligonucleotides for gene expression regulation","authors":"Wen-Da Chen , Liang Cheng","doi":"10.1016/j.tchem.2023.100051","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100051","url":null,"abstract":"<div><p>Cyclically caged oligonucleotides are a distinct category of altered biomacromolecules. They are created by incorporating caged motifs into oligonucleotides and subsequently undergoing cyclization through chemical or enzymatic means. The cyclic structure of these oligonucleotides significantly affects their characteristics and functionality, resulting in enhanced ribonuclease stability and loss of the ability to form complementary base pairs. However, when a specific stimulus is introduced, the ring structure can be deactivated, thereby restoring the oligonucleotide's function. This enables precise regulation of gene expression in both space and time by triggering a designated stimulus. In recent years, various cyclization strategies have been employed to modify antisense oligodeoxynucleotides, siRNAs, and gRNAs. This review will delve into the main synthesis methods used to generate cyclically caged oligonucleotides in the past decade. Moreover, we will explore the applications of these oligonucleotides in gene expression regulation, encompassing gene silencing and gene editing. This offers a valuable tool for comprehending the role of genes in the processes of biological growth and development.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100051"},"PeriodicalIF":0.0,"publicationDate":"2023-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X23000177/pdfft?md5=4f789c5fdb17e0af62268e3b37691309&pid=1-s2.0-S2666951X23000177-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92046279","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

Frustrated Lewis pair catalyzed C–F activation of α-trifluoromethylstyrenes 受挫Lewis对催化α-三氟甲基苯乙烯的C-F活化

Tetrahedron chem Pub Date : 2023-10-20 DOI: 10.1016/j.tchem.2023.100050

Chakyu Richard Chan , Dipendu Mandal , Rowan D. Young

引用次数: 0