Tetrahedron chem最新文献_第10页

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

When transition-metal-catalyzed C–H activation meets allene chemistry 当过渡金属催化的C–H活化满足烯化学时

Tetrahedron chem Pub Date : 2023-09-22 DOI: 10.1016/j.tchem.2023.100049

Shu-Meng Deng, Yu-Xuan Zhao, Chengming Wang

引用次数: 0

Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones 2-(4h-苯并[d][1,3]恶嗪-4-基)丙烯酸酯与2,4-二氢- 3h -吡唑-3-酮的有机催化区域和对映选择性(3+3)环化

Tetrahedron chem Pub Date : 2023-09-07 DOI: 10.1016/j.tchem.2023.100048

Zhongyue Lu, Xuling Chen, Pengfei Li

引用次数: 0

The seriatim Cu(I) activation of 1,1,1′,1′-tetrapinacolborylethane to prospective ring closing 1,1,1 '，1 ' -四聚氨基甲酸乙酯的连续Cu(I)活化对预期闭合环的影响

Tetrahedron chem Pub Date : 2023-08-22 DOI: 10.1016/j.tchem.2023.100045

Sara González , Dario Del Carratore , Ricardo J. Maza , Elena Fernández

引用次数: 0

Palladium-catalyzed ring-closing reaction of enynols with aminals via methylene transfer and C–N bond activation 钯催化烯醇与胺盐通过亚甲基转移和C–N键活化的闭环反应

Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100042

Bangkui Yu , Min Yu , Hanmin Huang

引用次数: 0

Organocatalytic activation of cyclopropanes in asymmetric synthesis 不对称合成环丙烷的有机催化活化

Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100041

Efraím Reyes, Uxue Uria, Liher Prieto, Luisa Carrillo, Jose L. Vicario

引用次数: 0

Palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated sp3 C–H bonds 钯(II)催化的级联反应由未激活的sp3 C-H键的定向激活引发

Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100046

Robbie Ge , Faith Herington , Alana Mangawang , Debabrata Maiti , Haibo Ge

{"title":"Palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated sp3 C–H bonds","authors":"Robbie Ge , Faith Herington , Alana Mangawang , Debabrata Maiti , Haibo Ge","doi":"10.1016/j.tchem.2023.100046","DOIUrl":"10.1016/j.tchem.2023.100046","url":null,"abstract":"<div><p>Cascade reactions—chemical processes consisting of two or more reactions in one pot—offer considerable advantages in terms of time, cost, atom efficiency, and reduced waste generation, and have thus unsurprisingly attracted considerable attention amongst the chemical community in recent decades. On the other hand, transition metal-catalyzed site-selective carbon-hydrogen (C–H) bond functionalization represents one of the most significant and efficient synthetic approaches in organic chemistry, enabling the conversion of common petroleum chemicals into highly valuable products in a single step. Utilization of this approach in cascades dramatically improves its applicability by allowing for the efficient construction of complex molecules from simple starting materials in a single pot. This perspective summarizes the developments in palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated aliphatic C–H bonds and our recent efforts in synthesizing bicyclic lactones, followed by current challenges and future opportunities.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100046"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46643525","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

Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols 手性反阴离子控制的金催化氢胺化/ β-氨基-1,4-烯醇对映选择性1,3-烯丙醇异构化的化学选择性

Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100043

L. Carli, Anyawan Tapdara, Jianwen Jin, Yichao Zhao, P. Chan

引用次数: 0