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Navigating Unexplored Territories of the Interrupted Ugi and Passerini Reactions toward Peptidomimetics
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.4c04810
Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis
{"title":"Navigating Unexplored Territories of the Interrupted Ugi and Passerini Reactions toward Peptidomimetics","authors":"Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis","doi":"10.1021/acs.orglett.4c04810","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04810","url":null,"abstract":"Interrupted reactions redirect established processes, often resulting in unexpected and novel outcomes. By employing a building block containing both acidic and oxo functionalities tethered to the same carbon, we uncovered interrupted variants of the Ugi and Passerini reactions. More than 20 derivatives with a peptide-like framework have been synthesized, demonstrating the broad scope and versatility of these reactions. Additional studies explored the use of various nucleophiles and postmodifications to expand even more the chemical diversity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"137 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427284","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
Cooperative Pd/Chiral Secondary Amine Enabled Diastereo- and Enantioselective [3 + 2] Cycloannulation: Synthesis of Polysubstituted Cyclopentanes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00007
Zuoqin Luo, Limei Gao, Dongqing He, Yuting Tian, Jikai Liu, Yongsheng Zheng
{"title":"Cooperative Pd/Chiral Secondary Amine Enabled Diastereo- and Enantioselective [3 + 2] Cycloannulation: Synthesis of Polysubstituted Cyclopentanes","authors":"Zuoqin Luo, Limei Gao, Dongqing He, Yuting Tian, Jikai Liu, Yongsheng Zheng","doi":"10.1021/acs.orglett.5c00007","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00007","url":null,"abstract":"A cooperative palladium/chiral amine enabled diastereo- and enantioselective [3 + 2] cycloaddition of π-allyl 1,3-dipoles with α,β-unsaturated aldehydes has been developed. A series of highly functionalized cyclopentanes bearing three continuous tertiary stereocenters can be facilely and efficiently obtained in good to excellent yields (51–97%) with synthetically useful diastereo- and enantioselectivity (93–99% ee) under mild reaction conditions. Control experiments and HRMS analyses were conducted to elucidate the possible mechanism. The utility of the current method was demonstrated by the gram-scale synthesis and elaboration of the products into various functionalized cyclopentanes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"69 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435697","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
Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00001
Lianyi Cao, Shihai Yan, Fangzhi Hu, Fei Wang, Shuai-Shuai Li, Mengzhe Pan, Yingkun Yan, Xiao-Mei Zhang
{"title":"Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes","authors":"Lianyi Cao, Shihai Yan, Fangzhi Hu, Fei Wang, Shuai-Shuai Li, Mengzhe Pan, Yingkun Yan, Xiao-Mei Zhang","doi":"10.1021/acs.orglett.5c00001","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00001","url":null,"abstract":"The TfOH-catalyzed dearomative [5 + 1] annulations were developed for the construction of chromane-fused spiroisoxazolines from readily available 5-amino-isoxazoles and <i>O</i>-alkyl <i>ortho</i>-oxybenzaldehydes. The “two-birds-with-one-stone” strategy featuring dearomatization of 5-amino-isoxazoles and α-C(sp<sup>3</sup>)–H bond functionalization of oxygen was disclosed via a cascade condensation/[1,5]-hydride transfer/dearomative spirocyclization process. In addition, the unprecedented direct dearomative spirocyclization of isoxazoles was achieved, which introduced a new family member of dearomative spirocyclization for dearomatization chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"16 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427285","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-Catalyzed Divergent Synthesis from o-Sulfonamido Trifluoroacetophenones and 2-En-4-ynyl Carbonates
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-15 DOI: 10.1021/acs.orglett.5c00269
Meng-Qi Gan, Jian-Xiang Zhu, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
{"title":"Palladium-Catalyzed Divergent Synthesis from o-Sulfonamido Trifluoroacetophenones and 2-En-4-ynyl Carbonates","authors":"Meng-Qi Gan, Jian-Xiang Zhu, Zhi-Chao Chen, Wei Du, Ying-Chun Chen","doi":"10.1021/acs.orglett.5c00269","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00269","url":null,"abstract":"Here we present a palladium-catalyzed divergent transformative reaction between <i>o-</i>sulfonamido trifluoroacetophenones and 2-en-4-ynyl carbonates. A spectrum of enantioenriched 2,5-dihydrofuran-fused tetrahydroquinolines bearing either a (<i>Z</i>)- or (<i>E</i>)-exocyclic double bond are constructed with moderate to high enantioselectivity from 5-aryl-substituted carbonates by tuning palladium sources, while analogous 2,3-dihydrofuran-fused products are furnished by using 5-alkyl-substituted ones.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"64 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418405","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
Ylide-Induced Ring Contraction of Coumarins to Benzofurans: Applications to the Synthesis of Bis-Heterocycles Ylide-Induced Ring Contraction of Coumarins to Benzofurans：双杂环合成的应用
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-15 DOI: 10.1021/acs.orglett.5c00079
Sandeep Kumar, Dinesh Kumar Gopalakrishnan, Shashank Shrotriya, Tarak Karmakar, Janakiram Vaitla
{"title":"Ylide-Induced Ring Contraction of Coumarins to Benzofurans: Applications to the Synthesis of Bis-Heterocycles","authors":"Sandeep Kumar, Dinesh Kumar Gopalakrishnan, Shashank Shrotriya, Tarak Karmakar, Janakiram Vaitla","doi":"10.1021/acs.orglett.5c00079","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00079","url":null,"abstract":"We report an unusual ring contraction of 4-chlorocoumarin to benzofuranoyl sulfoxonium ylides using a Corey-ylide. These stabilized ylides were subsequently utilized for the synthesis of various valuable <i>bis</i>-heterocycles under both metal and metal-free conditions. The synthetic utility of this method is illustrated through the synthesis of known bioactive compounds. Detailed mechanistic investigations and quantum chemical calculations have provided valuable insights into the mechanism of the ring contraction reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"48 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418404","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 Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons 2-Aminochalcones 和 5-Alkenyl-Thiazolones 的不对称 Aza-Michael/Michael/Mannich Domino 反应：获得对映体富集的 1,4-硫杂哌啶酮骨架
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-15 DOI: 10.1021/acs.orglett.4c04719
Zahid Ahmad Khan, Shweta Rohilla, Vinod K. Singh
{"title":"Asymmetric Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons","authors":"Zahid Ahmad Khan, Shweta Rohilla, Vinod K. Singh","doi":"10.1021/acs.orglett.4c04719","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04719","url":null,"abstract":"Herein, we disclose a novel organocatalytic approach for the enantioselective synthesis of 1,4-sulfur-bridged piperidinone skeletons via sequential aza-Michael/Michael/Mannich domino reaction of 2-aminochalcones and 5-alkenyl-thiazolones. The one-pot approach catalyzed by a bifunctional squaramide catalyst furnishes bridged polycyclic compounds with five contiguous stereocenters (three tertiary, two heteroquaternary) in excellent yields (up to 95%) and stereochemical outcomes (up to 99% ee and up to &gt;20:1 dr). The methodology offers outstanding control on regio- and chemoselectivity, showcasing broad substrate compatibility. Additionally, the reaction is scalable and postsynthetic transformation to a spirothiazolone-tetrahydroquinoline derivative further amplifies the synthetic utility of the methodology.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418424","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
Efficient Iron-Catalyzed Site/Regioselective Phosphinoylation of Carbohydrates.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.5c00143
Jie Zhao, Xiaorui Zhang, Qichang Yang, Tian Bi, Beichen Du, Jian Lv, Shuang-Xi Gu, Hai Dong
{"title":"Efficient Iron-Catalyzed Site/Regioselective Phosphinoylation of Carbohydrates.","authors":"Jie Zhao, Xiaorui Zhang, Qichang Yang, Tian Bi, Beichen Du, Jian Lv, Shuang-Xi Gu, Hai Dong","doi":"10.1021/acs.orglett.5c00143","DOIUrl":"10.1021/acs.orglett.5c00143","url":null,"abstract":"<p><p>The selective incorporation of phosphorus groups into sugar molecules holds substantial synthetic and biological significance, yet this area of research remains largely unexplored. In this study, we successfully devised a novel method employing an efficient Fe(III) catalyst for achieving site/regioselective phosphorylation/phosphinoylation of carbohydrates. This methodology boasts several merits, including mild reaction conditions, the employment of cost-effective and readily available catalysts, and exceptional selectivity. This approach provides new perspectives and valuable tools for the functional modification of sugar molecules.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1555-1560"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062308","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
Synthesis of Polyamides Bearing Directing Groups and Their Catalytic Depolymerization.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.4c04829
Ryota Shiraki, Yu-I Hsu, Hiroshi Uyama, Mamoru Tobisu
{"title":"Synthesis of Polyamides Bearing Directing Groups and Their Catalytic Depolymerization.","authors":"Ryota Shiraki, Yu-I Hsu, Hiroshi Uyama, Mamoru Tobisu","doi":"10.1021/acs.orglett.4c04829","DOIUrl":"10.1021/acs.orglett.4c04829","url":null,"abstract":"<p><p>We report a directing group (DG)-enabled strategy for polyamide depolymerization. Pyridine-based DGs selectively interact with In(III) catalysts, activating amide bonds for catalytic cleavage via alcoholysis. The process achieves efficient depolymerization of DG-introduced polyamides into recyclable monomers, providing a sustainable chemical recycling approach for robust polyamides.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1453-1458"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062409","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
3-Alkyl-1,2,4-triazines as Heterocyclic Platforms for Organocatalytic Enantioselective Benzylic C-H Functionalization.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI: 10.1021/acs.orglett.5c00008
Anthony Lapray, Marie-Aude Hiebel, Sylvain Oudeyer, Jean-François Lohier, Franck Suzenet, Jean-François Brière
{"title":"3-Alkyl-1,2,4-triazines as Heterocyclic Platforms for Organocatalytic Enantioselective Benzylic C-H Functionalization.","authors":"Anthony Lapray, Marie-Aude Hiebel, Sylvain Oudeyer, Jean-François Lohier, Franck Suzenet, Jean-François Brière","doi":"10.1021/acs.orglett.5c00008","DOIUrl":"10.1021/acs.orglett.5c00008","url":null,"abstract":"<p><p>The α-3-(1,2,4-triazine)-α-cyanoacetate derivatives exhibit a unique and well-defined dearomatized structure undergoing efficient organocatalytic aromatization-alkylation sequences with Michael acceptors in order to construct an all-carbon tetrasubstituted stereocenter with high ee values. These new players in the field of enantioselective catalytic benzylic C-H functionalization afford versatile molecular platforms toward the construction of valuable 3D-heterocycles.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1504-1510"},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143070778","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(II)-Catalyzed Regioselective Hydroamination of Allylamines to N-Alkyl Sulfoximines.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-14 DOI: 10.1021/acs.orglett.5c00316
Shib Nath Saha, Nityananda Ballav, Mahiuddin Baidya
{"title":"Palladium(II)-Catalyzed Regioselective Hydroamination of Allylamines to <i>N</i>-Alkyl Sulfoximines.","authors":"Shib Nath Saha, Nityananda Ballav, Mahiuddin Baidya","doi":"10.1021/acs.orglett.5c00316","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00316","url":null,"abstract":"<p><p>An intermolecular coupling between sulfoximines and allyl amines, linked to the picolinamide directing group, is developed by leveraging a nucleopalladation-guided regioselective hydroamination strategy, enabling the production of a range of valuable <i>N</i>-alkyl sulfoximines in high yields. The protocol features operational simplicity and a broad substrate scope and was also amenable to aniline nucleophiles. Synthetic utilities were showcased through scale-up reactions and product diversifications, leading to biorelevant molecules.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412400","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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