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Cycloadditions of Benzynes with the Azoxy [RN═N+(O-)R'] 1,3-Dipole Tautomer of 1-Hydroxybenzotriazole (HOBT). 苄炔与 1-羟基苯并三唑 (HOBT) 的氮氧 [RN═N+(O-)R'] 1,3-二极同系物的环加成反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c01819
Sangjun Lee, Thomas R Hoye
{"title":"Cycloadditions of Benzynes with the Azoxy [RN═N<sup>+</sup>(O<sup>-</sup>)R'] 1,3-Dipole Tautomer of 1-Hydroxybenzotriazole (HOBT).","authors":"Sangjun Lee, Thomas R Hoye","doi":"10.1021/acs.orglett.4c01819","DOIUrl":"10.1021/acs.orglett.4c01819","url":null,"abstract":"<p><p>1,3-Dipolar cycloadditions of azoxy species are rare. HOBT exists as a pair of tautomers, one of which contains an azoxy subunit. We show that heavily substituted, thermally generated benzynes react with HOBT by engaging the azoxy tautomer to give products having a benzotriazole with a benzyne-derived <i>o</i>-hydroxyaryl group at N2. DFT calculations were used to probe aspects of the mechanism. HOBT analogs of the uronium family (HBTU, HCTU, TATU, and HATU) react in an analogous fashion. The parent 1,2-dehydrobenzene (<i>o</i>-benzyne) generated by the action of (basic) CsF reacts with HOBT in an orthogonal manner to give, exclusively, an N1-arylated product.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464390","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
Nonactivated Aziridine Synthesis by Intermolecular Polarity-Mismatched Carboamination of Unactivated Alkenes with Unactivated Alkyl Halides. 通过未活化烯与未活化烷基卤化物的分子间极性错配羧基化合成非活化氮丙啶。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c01224
Linlin Wu, Lei Li, Yao Zhao, Jiacheng Rui, Ying Zhan, Ling Zhang, Rizhi Chen, Jianrong Steve Zhou, Chenjie Zhu, Xiaojin Wu
{"title":"Nonactivated Aziridine Synthesis by Intermolecular Polarity-Mismatched Carboamination of Unactivated Alkenes with Unactivated Alkyl Halides.","authors":"Linlin Wu, Lei Li, Yao Zhao, Jiacheng Rui, Ying Zhan, Ling Zhang, Rizhi Chen, Jianrong Steve Zhou, Chenjie Zhu, Xiaojin Wu","doi":"10.1021/acs.orglett.4c01224","DOIUrl":"10.1021/acs.orglett.4c01224","url":null,"abstract":"<p><p>A general intermolecular polarity-mismatched carboamination reaction of unactivated alkenes with unactivated alkyl halides has been developed. A series of nonactivated alkyl-substituted aziridines were constructed in exclusive regioselectivity. The dual polarity-mismatched mechanism might be involved.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464392","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
Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Cycloalkenes to Access Chiral 2-Aryl Tetralins. 铱催化未官能化环烯的不对称氢化反应以获得手性 2-芳基四氢萘。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c02054
Tierui Pan, Qianjia Yuan, Defeng Xu, Wanbin Zhang
{"title":"Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Cycloalkenes to Access Chiral 2-Aryl Tetralins.","authors":"Tierui Pan, Qianjia Yuan, Defeng Xu, Wanbin Zhang","doi":"10.1021/acs.orglett.4c02054","DOIUrl":"10.1021/acs.orglett.4c02054","url":null,"abstract":"<p><p>The transition-metal catalyzed asymmetric hydrogenation of unfunctionalized alkenes is challenging. Herein, we report an efficient iridium-catalyzed asymmetric hydrogenation of unfunctionalized cycloalkenes, delivering chiral 2-aryl tetralins in excellent yields and with moderate to excellent enantioselectivities. The reaction can be performed on a gram-scale with a low catalyst loading (S/C = 1000), and the reduced product was obtained without erosion of the enantioselectivity. Deuterium experiments indicated that the C═C bond in the substrate is hydrogenated directly without isomerization.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141475444","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
Anion-Relay Double Aza-Michael-Michael Cascades to Enone-Tethered Cyclohexadienones: Access to an Intricate Bridged Ring System. 阴离子-中继双 Aza-Michael-Michael 级联至 Enone-Tethered Cyclohexadienones:进入复杂的桥环系统。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-06-26 DOI: 10.1021/acs.orglett.4c01009
Anil Chauhan, Raj Kumar Patel, Akhilesh Yadav, Ruchir Kant, Ravindra Kumar
{"title":"Anion-Relay Double Aza-Michael-Michael Cascades to Enone-Tethered Cyclohexadienones: Access to an Intricate Bridged Ring System.","authors":"Anil Chauhan, Raj Kumar Patel, Akhilesh Yadav, Ruchir Kant, Ravindra Kumar","doi":"10.1021/acs.orglett.4c01009","DOIUrl":"10.1021/acs.orglett.4c01009","url":null,"abstract":"<p><p>An anion-relay double aza-Michael-Michael addition strategy has been reported for the synthesis of intricate scaffolds from enone-tethered cyclohexadienones and primary amines. This method discloses the base-catalyzed synthesis of highly valued bridged aza-tricyclic frameworks with a high level of product selectivity and stereoselectivity. Gram scale synthesis and synthetic transformation were shown to afford structurally diverse bridged aza-polycyclic amines. Control experiments and the kinetic profile were studied to determine a plausible reaction mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453748","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
Four-Component Radical 1,2-Selenosulfonylation of Allenes. 烯烃的四组分 1,2-硒磺酰化反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-06-27 DOI: 10.1021/acs.orglett.4c01798
Xiao-Rong Shu, Mu-Han Li, Cuiyan Wu, Xi-Ni Luo, Dong-Qing Yang, Ming-Qi Yang, Yue-Jiao Lu, Guo-Ping Ge, Jidan Liu, Wen-Ting Wei
{"title":"Four-Component Radical 1,2-Selenosulfonylation of Allenes.","authors":"Xiao-Rong Shu, Mu-Han Li, Cuiyan Wu, Xi-Ni Luo, Dong-Qing Yang, Ming-Qi Yang, Yue-Jiao Lu, Guo-Ping Ge, Jidan Liu, Wen-Ting Wei","doi":"10.1021/acs.orglett.4c01798","DOIUrl":"10.1021/acs.orglett.4c01798","url":null,"abstract":"<p><p>Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we have developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides for the synthesis of complex selenosulfones. This is the first case of achieving the 1,2-selenosulfonylation of allenes via a radical process, wherein precise control of radical rates and polarity matching enhance high regioselective conversion. The reaction conditions are ecofriendly and mild with step-efficiency by forming two new C-S bonds and one C-Se bond in one pot. Moreover, the 1,2-selenosulfonylation of allenes can be achieved by replacing cycloketone oxime esters with aryldiazonium tetrafluoroborates in this system.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453751","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 Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones. 铜催化炔烯丙基酯与蒽的远程不对称炔烯丙基取代。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c01916
Tao-Yan Lin, Meng-Die Li, Rui Wang, Xinru Wang
{"title":"Copper-Catalyzed Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones.","authors":"Tao-Yan Lin, Meng-Die Li, Rui Wang, Xinru Wang","doi":"10.1021/acs.orglett.4c01916","DOIUrl":"10.1021/acs.orglett.4c01916","url":null,"abstract":"<p><p>Anthrones are key structural motifs in many natural products and pharmaceutical chemicals. However, due to its unique tricyclic aromatic structure, the synthetic space for the development of chiral anthrone derivatives is largely limited. By utilizing the potential of the copper-catalyzed remote asymmetric yne-allylic substitution reaction, we describe the first example of copper-catalyzed highly regio- and enantioselective remote yne-allylic substitution on various yne-allylic esters with anthrones under a mild reaction condition, which afforded a range of enantioenriched 1,3-enynes with exhibiting broad functional group tolerance across 51 examples.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464389","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
Palladium/Norbornene Cooperatively Catalyzed Modular Trifunctionalization of 2-Bromoaryl Ketone via a Decarbonylation Process. 钯/降冰片烯通过脱羰基过程协同催化 2-溴芳基酮的模块化三官能化。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c01431
Qian Zhang, Yufeng Li, Xiaoliang Yang, Zeguo Fang, Dong Li
{"title":"Palladium/Norbornene Cooperatively Catalyzed Modular Trifunctionalization of 2-Bromoaryl Ketone via a Decarbonylation Process.","authors":"Qian Zhang, Yufeng Li, Xiaoliang Yang, Zeguo Fang, Dong Li","doi":"10.1021/acs.orglett.4c01431","DOIUrl":"10.1021/acs.orglett.4c01431","url":null,"abstract":"<p><p>Palladium/norbornene cooperatively catalyzed Catellani-type reactions were normally limited to aryl iodides as substrates. The employment of aryl bromides has remained challenging. Herein a Pd/NBE cooperatively catalyzed Catellani-type reaction of 2-bromoaryl ketone is described. The 2-bromoaryl ketone was employed as both substrates and arylation reagents with a Heck acceptor. A decarbonylation process of the ketones also occurred in the reaction, finishing the modular <i>ispo</i>-Heck/<i>ortho</i>,<i>ortho</i>-diarylation in one pot. It provided the functionalized <i>m</i>-triphenyl derivatives with three new C-C bonds in moderate to excellent yields which exhibited good regioselectivities and functional group tolerance.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464393","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
Silver-Catalyzed Decarboxylative Nitrooxylation of Aliphatic Carboxylic Acids. 银催化脂肪族羧酸的脱羧硝酰氧基化反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-07-01 DOI: 10.1021/acs.orglett.4c02180
Qian Yu, Donglin Zhou, Pingping Yu, Chunlan Song, Ze Tan, Jiakun Li
{"title":"Silver-Catalyzed Decarboxylative Nitrooxylation of Aliphatic Carboxylic Acids.","authors":"Qian Yu, Donglin Zhou, Pingping Yu, Chunlan Song, Ze Tan, Jiakun Li","doi":"10.1021/acs.orglett.4c02180","DOIUrl":"10.1021/acs.orglett.4c02180","url":null,"abstract":"<p><p>Here, we present a silver-catalyzed decarboxylative nitrooxylation via a radical-based approach. The substrate scope of this reaction prototype extends to nonactivated primary and secondary carboxylic acids. This protocol provides a practical method for the synthesis of an unprecedented family of organic nitrates and exhibits wide functional group compatibility. Preliminary mechanistic studies reveal that a high-valent silver(II) nitrate complex is a versatile NO<sub>3</sub> resource pool, allowing for facile C-O bond formation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141475446","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
The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy. 通过环辛二烯策略全合成金丝桃素。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 DOI: 10.1021/acs.orglett.4c01836
Julien A König, Bernd Morgenstern, Johann Jauch
{"title":"The Total Synthesis of Hyperfirin via a Cyclooctadiene Strategy.","authors":"Julien A König, Bernd Morgenstern, Johann Jauch","doi":"10.1021/acs.orglett.4c01836","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c01836","url":null,"abstract":"<p><p>Polycyclic polyprenylated acylphloroglucinols (PPAPs) combine compelling structural complexity with effective biological activity. The total synthesis of Hyperfirin is reported as one linear sequence. Key to this novel modular strategy is to access the bicyclo[3.3.1]nonane-2,4,9-trione framework via transannular acylation of a decorated eight-membered ring, followed by late stage bridgehead substitution. The described route adds flexibility to PPAP construction and broadens the scope of eight-membered ring chemistry.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597950","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
Stephaochratidin A, a Rare Stephacidin-Asperochratide Hybrid with Ferroptosis Inhibitory Activity from the Deep-Sea-Derived Aspergillus ochraceus. 赭曲霉毒素 A,一种罕见的赭曲霉毒素-赭曲霉内酯混合物,具有抑制深海赭曲霉铁突变的活性。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-07-12 Epub Date: 2024-06-24 DOI: 10.1021/acs.orglett.4c01745
Zheng-Biao Zou, Yan Li, Yuan Wang, Chun-Lan Xie, Ze-Qing Li, Shan-Shan Nie, You Li, Si-Yu Fang, Tian-Hua Zhong, Li-Sheng Li, Xian-Wen Yang
{"title":"Stephaochratidin A, a Rare Stephacidin-Asperochratide Hybrid with Ferroptosis Inhibitory Activity from the Deep-Sea-Derived <i>Aspergillus ochraceus</i>.","authors":"Zheng-Biao Zou, Yan Li, Yuan Wang, Chun-Lan Xie, Ze-Qing Li, Shan-Shan Nie, You Li, Si-Yu Fang, Tian-Hua Zhong, Li-Sheng Li, Xian-Wen Yang","doi":"10.1021/acs.orglett.4c01745","DOIUrl":"10.1021/acs.orglett.4c01745","url":null,"abstract":"<p><p>One rare stephacidin-asperochratide hybrid, stephaochratidin A (<b>1</b>), was isolated from the deep-sea-derived <i>Aspergillus ochraceus</i> MCCC 3A00521. The relative structure of <b>1</b> was determined by comprehensive analyses of its 1D and 2D NMR data as well as HRESIMS data. And the absolute configuration was unambiguously assigned by ECD calculations and the X-ray single-crystal diffraction analysis. Plausible biosynthetic pathway of <b>1</b> was proposed. Stephaochratidin A (<b>1</b>) exhibited significant ferroptosis inhibitory activity with the EC<sub>50</sub> value of 15.4 μM by downregulating HMOX-1 expression and lipid peroxidation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141441753","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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