Organic chemistry frontiers : an international journal of organic chemistry最新文献_第7页

Condition-controlled selective synthesis of spiroisoquinolinones or spiroisoindolinones via CHA–initiated spiroannulation, ring opening and ring contraction† 通过CHA启动的旋环形成、环开和环收缩，条件控制选择性合成螺异喹啉酮或螺异吲哚酮

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5qo00257e

Yujing Xiao , Yuanshuang Xu , Shuya Zhang , Xinying Zhang , Xuesen Fan

{"title":"Condition-controlled selective synthesis of spiroisoquinolinones or spiroisoindolinones via CHA–initiated spiroannulation, ring opening and ring contraction†","authors":"Yujing Xiao , Yuanshuang Xu , Shuya Zhang , Xinying Zhang , Xuesen Fan","doi":"10.1039/d5qo00257e","DOIUrl":"10.1039/d5qo00257e","url":null,"abstract":"<div><div>Presented herein is a condition-controlled selective synthesis of isoindole spiroisoquinolinone or isoindole spiroisoindolinone derivatives based on the cascade reactions of 3-phenylisoxazolone with diazo homophthalimide. When the reaction was carried out in the presence of Rh(<span>iii</span>) and NaOAc under argon for 1 h, the former was obtained <em>via</em> C–H activation-initiated formal [4 + 1] spiroannulation and isoxazolone ring opening. When the reaction was carried out in the presence of Rh(<span>iii</span>) and KOAc under air for 12 h, the latter was obtained <em>via</em> [4 + 1] spiroannulation, isoxazolone ring opening and isoquinolinone ring contraction. With this method, concise and effective synthesis of two classes of valuable spirocyclic products from the same starting materials was achieved by simply tuning the reaction conditions. In general, this protocol features easily controllable selectivity, oxidizing and transformable directing group, redox-neutral conditions, unique reaction pathway and good functional group compatibility. The methodology is readily scalable and the structure of the product thus obtained could be diversely decorated.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3880-3886"},"PeriodicalIF":0.0,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143672301","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

Three-component, stereoselective C–N bond forming alkene difunctionalization 三组分立体选择性C-N键形成烯烃双官能化

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5qo00160a

Jihoon Na , Je Uk Kim , Seonggyu Kim , Chanwoo Kim , Gayoung Lee , Sumin Lee

{"title":"Three-component, stereoselective C–N bond forming alkene difunctionalization","authors":"Jihoon Na , Je Uk Kim , Seonggyu Kim , Chanwoo Kim , Gayoung Lee , Sumin Lee","doi":"10.1039/d5qo00160a","DOIUrl":"10.1039/d5qo00160a","url":null,"abstract":"<div><div>Amines are essential functional groups in pharmaceuticals, agrochemicals, and bioactive molecules, with C(sp<sup>3</sup>)–N bonds playing a crucial role in enhancing biological activity and selectivity. Alkene difunctionalization offers a powerful strategy for constructing these bonds by introducing two distinct functional groups across a double bond in a single step. While two-component alkene difunctionalization has been widely studied, general three-component strategies for amine synthesis remain underdeveloped due to challenges in controlling regioselectivity, stereoselectivity, and competing side reactions. Recent advancements have addressed these limitations through transition-metal catalysis, directing-group-free methodologies, and radical-based mechanisms, enabling stereoselective synthesis of amines from readily available starting materials. This review discusses emerging strategies in three-component, stereoselective C–N bond-forming alkene difunctionalization, emphasizing mechanistic innovations and their impact on synthetic organic chemistry.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3896-3919"},"PeriodicalIF":0.0,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143758666","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

Photoredox-catalyzed three-component alkylation of glycine derivatives and peptides via a site-selective 1,5-hydrogen atom transfer cascade† 通过位置选择性1,5-氢原子转移级联，光氧化还原催化甘氨酸衍生物和多肽的三组分烷基化

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-04-02 DOI: 10.1039/d5qo00294j

Hongying Fan , Liulin Jiao , Ting Yuan , Jian Chen , Qingyun Gu , Xue Zhang , Jinyu Hou , Zhongzhen Yang , Li Guo , Yong Wu

引用次数: 0

Palladium(ii)-catalyzed enantioselective desymmetrization ring opening of oxabicyclic alkenes with alkynylanilines: efficient access to enantioenriched functionalized cyclohexenes† 钯（II）催化氧三环烯烃与烷基苯胺的对映选择性去对称开环：对映富集功能化环己烯的有效途径

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00118h

Binhong Tan , Junjie Meng , Qianru Liu , Shixin Chen , Mingyue Xue , Yue Zhang , Yuping Zhang , Zhaodong Li

引用次数: 0

Understanding the reaction mechanism of anti-addition of (NHC)Au(i)–H and (NHC)Au(i)–F across alkyne† （NHC）Au(I)-H和（NHC）Au(I)-F跨炔反加成反应机理的研究

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00432b

Wing Chun Chan , Zhenyang Lin

引用次数: 0

Oxetane as a part of modern medicinal chemistry toolbox: the advanced synthesis of 3,3-disubstituted building blocks† Oxetane作为现代药物化学工具箱的一部分：3,3-二取代构建块的高级合成

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00572h

Eduard V. Litskan , Oleksandr V. Semenchenko , Serhii V. Lynnyk , Dmitry S. Granat , Bohdan V. Vashchenko , Anastasiia Ye. Hoida , Daria A. Tolmachova , Dmytro O. Leha , Oleksandr O. Grygorenko , Dmytro M. Volochnyuk , Serhiy V. Ryabukhin

{"title":"Oxetane as a part of modern medicinal chemistry toolbox: the advanced synthesis of 3,3-disubstituted building blocks†","authors":"Eduard V. Litskan , Oleksandr V. Semenchenko , Serhii V. Lynnyk , Dmitry S. Granat , Bohdan V. Vashchenko , Anastasiia Ye. Hoida , Daria A. Tolmachova , Dmytro O. Leha , Oleksandr O. Grygorenko , Dmytro M. Volochnyuk , Serhiy V. Ryabukhin","doi":"10.1039/d5qo00572h","DOIUrl":"10.1039/d5qo00572h","url":null,"abstract":"<div><div>Despite numerous potential advantages of oxetanes, their restricted synthetic accessibility and propensity to ring-opening hamper their wide application in drug design. In this work, we disclose our experimental achievements and 10 years of experience in oxetane chemistry and provide a comprehensive study on the oxetane core tolerance towards the reaction conditions of the typical toolbox of organic and medicinal chemists, which is based on our original, unpublished developments. The scope of examined reactions includes oxidation, reduction, alkylation, acylation, nucleophilic substitution, C–C/CC/CC bond formation, hydrolysis, and protecting groups cleavage, and demonstrates the stability of the oxetane's moiety towards acidic and basic conditions. Over 40 transformations were applied to generate the oxetane chemical stability profile, which could direct the design of other synthetic approaches for the synthesis and incorporation of oxetanes in the future. The additional aim of the work included the optimization of the synthetic protocols with the possibility of scaling up to 1 kg in a single run. Newly designed synthetic protocols in our hands allowed for the preparation of novel 3,3-disubstituted oxetanes as small building blocks (over 100 examples, almost 90% of which were not reported previously in the literature). These results benefit the development of oxetanes as a part of the toolbox of modern medicinal chemistry, as well as their incorporation into drug development programs.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3775-3785"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862519","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

Visible-light-induced radical cascade cyclization of 2-isocyanobiaryls via 1,5-hydrogen atom transfer (1,5-HAT)† 可见光诱导的1,5-氢原子转移（1,5- hat）自由基级联环化2-异氰基

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00031a

Yafei Zhu , Penghua Zhang , Xingqin Tian , Xueqin Wang , Mi Wang , Cuimei Zhang , Jian Chen , Jing Zhang , Guanghui Lv , Yong Wu

引用次数: 0

Asymmetric oxidative rearrangement of indoles enabled by dual catalysis with in situ generated acyl hypoiodite and chiral phosphoric acid† 用原位生成的酰基次碘酸盐和手性磷酸双重催化实现吲哚的不对称氧化重排

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00302d

Haowei Gao , Xihui Yang , Lei Shi

{"title":"Asymmetric oxidative rearrangement of indoles enabled by dual catalysis with in situ generated acyl hypoiodite and chiral phosphoric acid†","authors":"Haowei Gao , Xihui Yang , Lei Shi","doi":"10.1039/d5qo00302d","DOIUrl":"10.1039/d5qo00302d","url":null,"abstract":"<div><div>Although oxidative halogenation approaches have reached remarkable levels of sophistication, reports on the use of inorganic halides as pre-catalysts for the asymmetric synthesis of enantioenriched molecules have remained elusive. Herein, we disclose a dual-catalytic strategy for achieving a mild and enantioselective protocol for the synthesis of optically active oxindoles <em>via</em> the oxidative rearrangement of indoles. The proper choice of the oxidant–halide system and the chiral catalyst employed is crucial for high reactivity and enantioselectivity. Mechanistic studies indicate that acyl hypoiodite as the key active species to react with indoles is generated catalytically <em>in situ</em> and chiral phosphoric acid functions as an efficient resolving catalyst for the corresponding dynamic kinetic resolution of the resultant 3-iodo indolenines. The successful execution of the dual-catalytic strategy triggered by the utilization of halonium intermediates as traceless handles provides a significant conceptual advantage and will serve as a useful foundation for further investigations into cooperative stereocontrolled halide-catalyzed transformations.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3848-3855"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723997","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

Garynthone A–I, PPAPs with diverse skeletons isolated from Garcinia yunnanensis and their immunosuppressive activity† Garynthone A-I、云南藤黄不同骨架PPAPs及其免疫抑制活性研究

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00414d

Zifeng Guo , Pengxue Ji , Shengnan Yang , Zhiyuan Li , Yongbo Yu , Jingming Jia , Anhua Wang

引用次数: 0

Expedient access to α-(hetero)aryl-α-keto-1,3-diamines via redox-neutral photocatalyzed reactions of N-vinylimides with α-aminoalkyl radicals† 通过氧化还原中性光催化n -乙烯酰亚胺与α-氨基烷基自由基的反应，方便地获得α-（杂）芳基-α-酮-1,3-二胺

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00239g

Yu Zhao , Yutao Jing , Yan Li , Li Qiu , Yewen Fang

引用次数: 0