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Correction to "Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation". 对“通过单电子C-O活化镍催化缩醛与酸酐和三氟酸乙烯酯的还原偶联”的修正。
IF 5 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03807
Eunbi Kim, Meredith A Borden, Junha Hwang, Abigail G Doyle, Sun Dongbang
{"title":"Correction to \"Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation\".","authors":"Eunbi Kim, Meredith A Borden, Junha Hwang, Abigail G Doyle, Sun Dongbang","doi":"10.1021/acs.orglett.5c03807","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03807","url":null,"abstract":"","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":5.0,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145190460","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Three-Component Cyclization/Haloazidation of Bicyclo[1.1.0]butane-1-carboxamides: Construction of Halogenated Spiro[cyclobutane-1,3'-quinolin]-2'-one Derivatives. 双环[1.1.0]丁烷-1-羧酰胺的三组分环化/卤代化：卤代螺[环丁烷-1,3'-喹啉]-2'- 1衍生物的构建。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03545
Jiyao Liu,Yuchen Rong,Jing Yang,Yang Jiao,Yun Liu,Xiaoqin Liu,Liangce Rong
{"title":"Three-Component Cyclization/Haloazidation of Bicyclo[1.1.0]butane-1-carboxamides: Construction of Halogenated Spiro[cyclobutane-1,3'-quinolin]-2'-one Derivatives.","authors":"Jiyao Liu,Yuchen Rong,Jing Yang,Yang Jiao,Yun Liu,Xiaoqin Liu,Liangce Rong","doi":"10.1021/acs.orglett.5c03545","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03545","url":null,"abstract":"A new BCB-type substrate to assemble halogenated spiro[cyclobutane-1,3'-quinolin]-2'-one derivatives via a radical cascade strain-release cyclization reaction has been successfully developed. The reaction features broad substrate scope, mild reaction conditions, and separated diastereomers. Importantly, the reaction time is very short (3-5 min), leading to this strategy being highly time-efficient and practical value.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"69 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189238","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 N–O-Linked α-N-Acetylgalactosaminoglycosides via Oxime O-Glycosylation with 2-Nitrogalactals 肟o糖基化与2-硝基半乳糖立体选择性合成n - o链α- n -乙酰半乳糖氨基糖苷
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03416
Yiyang Cheng, Shuhui Lei, Xiaoxue Tao, Yujuan Wang, Zhen Zhou, Yuanwei Dai
{"title":"Stereoselective Synthesis of N–O-Linked α-N-Acetylgalactosaminoglycosides via Oxime O-Glycosylation with 2-Nitrogalactals","authors":"Yiyang Cheng, Shuhui Lei, Xiaoxue Tao, Yujuan Wang, Zhen Zhou, Yuanwei Dai","doi":"10.1021/acs.orglett.5c03416","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03416","url":null,"abstract":"GalNAc-type <i>O</i>-glycosylation is an essential post-translational modification that plays fundamental roles in various biological processes. N–O-linked glycosidic linkages are desirable and practical mimetics of native <i>O</i>-glycosidic bonds. However, efficient construction of α-aminooxy GalNAc linkages remains challenging. Herein, we present a highly stereoselective oxime <i>O</i>-glycosylation of 2-nitroglycal promoted by a substoichiometric amount of <i>t</i>-BuOLi, enabling efficient access to a broad spectrum of N–O-linked α-GalNAc glycosides. This approach features an excellent yield and α-selectivity, broad substrate scope, and easy scalability. The synthetic applications of this method are illustrated by the late-stage glycosylation of structurally complex drug molecules and diverse precise synthetic transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Copper-Catalyzed Diastereoselective Defluoroborylation of Pentafluoroethyl Alkenes Using (pin)B-B(dan). 铜催化（pin）B-B（dan）对五氟乙基烯烃的非对映选择性去氟硼化反应。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03558
Yihan Tang,Gavin Chit Tsui
{"title":"Copper-Catalyzed Diastereoselective Defluoroborylation of Pentafluoroethyl Alkenes Using (pin)B-B(dan).","authors":"Yihan Tang,Gavin Chit Tsui","doi":"10.1021/acs.orglett.5c03558","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03558","url":null,"abstract":"We herein describe a highly diastereoselective Cu(I)-catalyzed defluoroborylation of pentafluoroethyl alkenes using a diboron reagent (pin)B-B(dan). When 1,1- or 1,2-disubstituted pentafluoroethyl alkenes are employed as substrates, tetra- or trisubstituted fluoroalkenes can be obtained, respectively, in up to >99:1 diastereoselectivity. This protocol provides access to novel allyl-B(dan) compounds and allylic alcohols with alkene moieties containing F and CF3 on the same carbon.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188836","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes 光照射促进1-芳基三嗪的异氮化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03938
Takashi Niwa, Yamato Ezo, Satoshi Fukuda, Kenji Watanabe, Isao Kii, Takamitsu Hosoya
{"title":"Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes","authors":"Takashi Niwa, Yamato Ezo, Satoshi Fukuda, Kenji Watanabe, Isao Kii, Takamitsu Hosoya","doi":"10.1021/acs.orglett.5c03938","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03938","url":null,"abstract":"Ultraviolet (UV) irradiation (λ<sub>max</sub> = 370 nm) of a methanol solution of 1-aryltriazenes and azidotrimethylsilane promotes ipso-azidation. Optimization of the reaction conditions and a mechanistic study revealed that the hydrazoic acid generated in situ enabled efficient transformation. The high functional group tolerance of this reaction allowed for the transformation of a broad range of 1-aryltriazenes, including those introduced on a protein, to the corresponding aryl azides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145189544","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Pyrazine-Linked End-Functionalized Helicenes: Impact of π-Extension on Frontier Orbital Localization and Chiroptical Properties. 吡嗪链末端功能化螺旋烯：π-延伸对前沿轨道定位和热学性质的影响。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03620
Zheng Zhang,Zhibo Liu,Takashi Hirose
{"title":"Pyrazine-Linked End-Functionalized Helicenes: Impact of π-Extension on Frontier Orbital Localization and Chiroptical Properties.","authors":"Zheng Zhang,Zhibo Liu,Takashi Hirose","doi":"10.1021/acs.orglett.5c03620","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03620","url":null,"abstract":"Control of chiroptical responses in π-conjugated molecules is critical for the design of chiral materials. We synthesized terminal π-extended helicenes linked by a pyrazine bridge and investigated their circular dichroism. Extension from naphthalene to tetracene decreased the S0 → S1 dissymmetry factors from 0.027 to nearly zero. TD-DFT calculations and our transition-moment density analysis revealed that frontier orbital localization on the helicene moiety is essential to achieving large g values, clarifying the origin of strong chiroptical activity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"33 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Nickel-Catalyzed C(sp3)-C(sp3) Coupling of Cyclopropanols via α-Bimetalloid Radicals: Access to γ-Carbonyl gem-Bis(boronates) and gem-Silylboronate Esters. 镍催化的C(sp3)-C（sp3）环丙醇通过α-双金属自由基偶联：获得γ-羰基宝石双（硼酸酯）和宝石硅硼酸酯。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-29 DOI: 10.1021/acs.orglett.5c03886
Linfei Zhu,Xueyu Zhang,Hui Wang
{"title":"Nickel-Catalyzed C(sp3)-C(sp3) Coupling of Cyclopropanols via α-Bimetalloid Radicals: Access to γ-Carbonyl gem-Bis(boronates) and gem-Silylboronate Esters.","authors":"Linfei Zhu,Xueyu Zhang,Hui Wang","doi":"10.1021/acs.orglett.5c03886","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03886","url":null,"abstract":"Herein, we disclose an efficient nickel-catalyzed C(sp3)-C(sp3) coupling reaction of ambiphilic reagents with cyclopropanols, enabling direct access to a range of synthetically valuable γ-carbonyl gem-diboronates and γ-carbonyl gem-silylboronate esters in good yields. This method shows broad substrate scope and excellent functional group tolerance for cyclopropanols. Mechanistic studies indicate the involvement of α-bimetalloid radicals, and the resulting Bpin groups in products offer versatile handles for further derivatization.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"33 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145188857","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Synthetic Studies of Spiroschincarins: Construction of 1-Oxaspiro[6.6]tridecanone Skeleton with All-cis Cyclopropane Moiety. 螺旋体毒素的合成研究：含顺式环丙烷部分的1- oxspiro[6.6]三醇酮骨架的构建。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-28 DOI: 10.1021/acs.orglett.5c03325
Tetsushi Suzuki,Ryotaro Yagita,Kazuhiro Irie,Chihiro Tsukano
{"title":"Synthetic Studies of Spiroschincarins: Construction of 1-Oxaspiro[6.6]tridecanone Skeleton with All-cis Cyclopropane Moiety.","authors":"Tetsushi Suzuki,Ryotaro Yagita,Kazuhiro Irie,Chihiro Tsukano","doi":"10.1021/acs.orglett.5c03325","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03325","url":null,"abstract":"Spiroschincarins are triterpenoids characterized by a hexacyclic structure with a unique 1-oxaspiro[6.6]tridecanone skeleton and an all-cis substituted cyclopropane moiety. In the present study, this core skeleton was convergently synthesized by coupling all-cis-substituted cyclopropane and cycloheptanone fragments. The keys for its construction were the use of a conformationally limited substrate for lactonization and control of chelation for reducing the double bond on the spiro-lactone ring.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182666","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 π-Enriched Conjugated Dienynals via Photochemical Alkynyl Carbene Insertion into Furans. 光化学炔基卡宾插入呋喃立体选择性合成富π共轭二烯醚。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-28 DOI: 10.1021/acs.orglett.5c03085
Paru Jamwal,Ritik Shukla,Ramani Gurubrahamam
{"title":"Stereoselective Synthesis of π-Enriched Conjugated Dienynals via Photochemical Alkynyl Carbene Insertion into Furans.","authors":"Paru Jamwal,Ritik Shukla,Ramani Gurubrahamam","doi":"10.1021/acs.orglett.5c03085","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03085","url":null,"abstract":"The first photochemical carbene insertion reaction into furans is developed for the stereoselective synthesis of π-extended conjugated dienynal and dienynone scaffolds. The protocol harnesses sustainable visible light and does not demand any additives or photocatalysts. It provides a wide variety of densely functionalized dienynal/dienynone carboxylates in good yields with excellent selectivity (40 examples, up to 83% yield and (2E, 4E)-isomer). Furthermore, the developed strategy is scalable, and the downstream transformations are demonstrated toward obtaining valuable products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"398 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182668","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Asymmetric Synthesis of the Pentacyclic Framework of Kopsia Alkaloids. Kopsia生物碱五环骨架的不对称合成。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-09-28 DOI: 10.1021/acs.orglett.5c03771
Yeonghun Song,John Park,Sanghee Kim
{"title":"Asymmetric Synthesis of the Pentacyclic Framework of Kopsia Alkaloids.","authors":"Yeonghun Song,John Park,Sanghee Kim","doi":"10.1021/acs.orglett.5c03771","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03771","url":null,"abstract":"Pyrroloazocine alkaloids from the Kopsia genus exhibit structural complexity and pharmacological potential. We report the concise and asymmetric synthesis of a pentacyclic core from l-proline. The key features include a C-N-C chirality transfer process to prepare the α-tertiary amine intermediate enantioselectively, an eight-membered C ring-forming Friedel-Crafts reaction at the indole C3 position, and a dearomative indole-Claisen rearrangement to form a bridged pentacyclic scaffold. This study provides a versatile platform for the divergent synthesis of diverse Kopsia alkaloids.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"106 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182570","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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