The Journal of Organic Chemistry最新文献

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Origins of Diastereoselectivity in the Addition of Enoxysilanes to Vinyl Diazonium Salts 烯氧硅烷与乙烯基重氮盐的非对映选择性加成的起源
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-13 DOI: 10.1021/acs.joc.4c00874
Avery Peck, Manman Sun, Evan Howard, Xin Hong, Matthias Brewer
{"title":"Origins of Diastereoselectivity in the Addition of Enoxysilanes to Vinyl Diazonium Salts","authors":"Avery Peck, Manman Sun, Evan Howard, Xin Hong, Matthias Brewer","doi":"10.1021/acs.joc.4c00874","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00874","url":null,"abstract":"The addition of enoxysilanes to vinyl diazonium ions occurs with varying levels of diastereoselectivity. To understand the origins of the stereoselectivity, we studied these transformations using density functional theory (DFT) calculations. The selectivity stems from a stabilizing cation-π interaction that orients the nucleophile and the diazonium ion.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141602873","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction. 通过基于异氰酸酯的三组份反应构建多种融合色烯框架
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c01142
Yu-Wei He, Li Huang, Kun Huang, Chao-Guo Yan, Jing Sun, Ying Han
{"title":"Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction.","authors":"Yu-Wei He, Li Huang, Kun Huang, Chao-Guo Yan, Jing Sun, Ying Han","doi":"10.1021/acs.joc.4c01142","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01142","url":null,"abstract":"<p><p>A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing <i>o</i>-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(<i>o</i>-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro[cyclobuta[<i>c</i>]chromene-1,3'-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(<i>o</i>-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2',1':5,6]pyrano[3,4-<i>c</i>]chromene derivatives in high yields and with high diastereoselectivity.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589016","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Construction of Ethenyl-Substituted Acyclic Quaternary Stereocenters at the α-Position of Carbonyl Surrogates via Stereoselective Sulfonylvinylation-Reductive Desulfonylation. 通过立体选择性磺酰基乙烯化-还原脱磺作用,在羰基代用品的 α 位不对称地构建乙烯基取代的环状季态立体中心。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c01235
Nuermaimaiti Yisimayili, Chong-Dao Lu
{"title":"Asymmetric Construction of Ethenyl-Substituted Acyclic Quaternary Stereocenters at the α-Position of Carbonyl Surrogates via Stereoselective Sulfonylvinylation-Reductive Desulfonylation.","authors":"Nuermaimaiti Yisimayili, Chong-Dao Lu","doi":"10.1021/acs.joc.4c01235","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01235","url":null,"abstract":"<p><p><i>N</i>-Sulfinyl metalloenamines, derived from geometry-defined β,β-disubstituted enesulfinamides, undergo conjugate addition-elimination reaction with β-tosyl nitroolefin to afford α-sulfonylvinylated ketimines with high stereocontrol. Further desulfonylation using sodium naphthalenide gives carbonyl surrogates bearing a less-accessible acyclic quaternary α-stereocenters substituted with an ethenyl group and two sterically and electronically similar groups (e.g., methyl and ethyl). Synthetic application of the described protocol was demonstrated by enantioselective synthesis of (<i>S</i>)-bakuchiol.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589015","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
From Building Blocks to Catalysts: The Underinvestigated Potential of Boronic Acid Esters. 从积木到催化剂:硼酸酯的潜力尚未得到充分研究。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c00775
Ava Bousselat, Jacques Rouden, Jérôme Blanchet
{"title":"From Building Blocks to Catalysts: The Underinvestigated Potential of Boronic Acid Esters.","authors":"Ava Bousselat, Jacques Rouden, Jérôme Blanchet","doi":"10.1021/acs.joc.4c00775","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00775","url":null,"abstract":"<p><p>Lewis acids are crucial in chemistry, with applications in pharmaceuticals, agrochemicals, and materials science. In main-group chemistry, they offer alternatives to transition metals, prompting our study of halogenated boronic acid esters (BAEs). Although BAEs are well-known, their catalytic potential has been overlooked. Our investigation found their Lewis acidity superior to that of boron trifluoride and comparable to that of tris(pentafluorophenyl)borane. Additionally, their catalysis of the Sakurai allylation of aldehydes has been documented, paving the way for future advancements.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589019","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Iron(III)-Catalyzed Amine-Release Triple Condensation of Enaminones to C3-Alkenylated Dihydroquinolinones. 铁(III)催化的胺释放烯酮到 C3-烯基二氢喹啉酮的三重缩合。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c00750
Qiaoqiao Wang, Xu Yuan, Haoyang Sun, Jimei Yang, Xingjiang Yang, Jun Lin, Yi Jin
{"title":"Iron(III)-Catalyzed Amine-Release Triple Condensation of Enaminones to C3-Alkenylated Dihydroquinolinones.","authors":"Qiaoqiao Wang, Xu Yuan, Haoyang Sun, Jimei Yang, Xingjiang Yang, Jun Lin, Yi Jin","doi":"10.1021/acs.joc.4c00750","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00750","url":null,"abstract":"<p><p>C3-functionalized dihydroquinolinones represent a class of important biologically active compounds. Although methods for synthesizing C2/4-functionalized dihydroquinolinones have been extensively reported, research on the synthesis of C3-functionalized dihydroquinolinone is extremely rare. Herein, we report for the first time a method for C3-alkenylated dihydroquinolinones via iron(III)-catalyzed amine-release triple condensation of enaminones. These reactions exhibit broad substrate scope and offer operationally simple, low-cost catalyzed procedures in a single step. Subsequent intramolecular and intermolecular additions to the alkene moiety provide diverse C3-functionalized dihydroquinolinone derivatives.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597951","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Cu-Catalyzed Asymmetric Arylation of Enone Diesters with Arylboronic Acids. 铜催化的烯酮二酯与芳基硼酸的不对称芳基化反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c01045
Noritaka Kunitomo, Taichi Kano
{"title":"Cu-Catalyzed Asymmetric Arylation of Enone Diesters with Arylboronic Acids.","authors":"Noritaka Kunitomo, Taichi Kano","doi":"10.1021/acs.joc.4c01045","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01045","url":null,"abstract":"<p><p>The Cu-catalyzed asymmetric conjugate addition of arylboronic acids to enone diesters is reported. This operationally simple and scalable reaction proceeded under mild conditions. The practical utility of this approach was demonstrated by the synthesis of structurally important γ-lactones and a cyclopentene that bear an aryl group. Mechanistic studies revealed that two different copper catalytic species work synergistically in the reaction.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589018","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Selective Benzylic C-H Alkylation of Aromatic Sulfonamides with Maleimides. 钯催化的芳香族磺酰胺与马来酰亚胺的选择性苄基 C-H 烷基化反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c00850
Trisha Chakraborty, Gouranga Naskar, Masilamani Jeganmohan
{"title":"Palladium-Catalyzed Selective Benzylic C-H Alkylation of Aromatic Sulfonamides with Maleimides.","authors":"Trisha Chakraborty, Gouranga Naskar, Masilamani Jeganmohan","doi":"10.1021/acs.joc.4c00850","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00850","url":null,"abstract":"<p><p>An efficient method for the selective benzylic C-H alkylation of sulfonamides using maleimides has been developed. The reaction proceeds <i>via</i> the benzylic C(sp<sup>3</sup>)-H bond activation of sulfonamide in the presence of a Pd(II) catalyst without requiring any oxidant, additive, or external ligand. This methodology is highly compatible with a wide variety of substituted maleimides. A plausible reaction mechanism is also proposed to account for this alkylation reaction.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589021","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study NHC 催化 α-溴烯醛和 5-氨基异噁唑的 [3 + 3] 嵌合反应中的区域和立体选择性的机理和起源:DFT 研究
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c00980
Mingchao Zhang, Zhiqiang Zhang, Yan Li
{"title":"Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study","authors":"Mingchao Zhang, Zhiqiang Zhang, Yan Li","doi":"10.1021/acs.joc.4c00980","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00980","url":null,"abstract":"Density functional theory (DFT) calculations were conducted to explore the mechanisms and origins of regio- and stereoselectivities underlying the [3 + 3] annulation reaction between α-bromoenals and 5-aminoisoxazoles with <i>N</i>-heterocyclic carbene (NHC) as the catalyst. The reaction occurs in nine steps: (1) nucleophilic addition of NHC to α-bromoenal, (2) Breslow intermediate formation through 1,2-proton transfer, (3) debromination, (4) α,β-unsaturated acyl azolium intermediate formation via 1,3-proton transfer, (5) addition of α,β-unsaturated acyl azolium intermediate to 5-aminoisoxazole, (6) deprotonation, (7) protonation, (8) ring closure, and (9) elimination of NHC. For the fifth step, 1,2-addition suggested in the experiment was not supported by our results. Instead, we found that Michael addition is energetically the most feasible pathway and the stereo-controlling step that preferentially provides the S-configuration product. DFT-computed results and experimental findings agree well. Analysis of distortion/interaction reveals that lower distortion energy leads to stability of the transition state corresponding to the S-configuration product. Global reactivity index analysis indicates that the behavior of the NHC catalyst differs significantly before and after the Breslow intermediate debromination. Before debromination, the nucleophilicity of α-bromoenal is enhanced by addition to NHC. However, after debromination, the α,β-unsaturated acyl azole generates and acts as an electrophilic reagent.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597391","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Fully Substituted Difluoromethylpyrazoles by Cyclization of Difluoroacetohydrazonoyl Bromides with 2-Acylacetonitriles or Malononitrile. 通过二氟乙酰基吡唑酰溴与 2-酰基乙腈或丙二腈的环化反应合成全取代的二氟甲基吡唑。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-12 DOI: 10.1021/acs.joc.4c00828
Si-Wei Wang, Jianzhong Zhang, Zhoubin Deng, Yuyu Lv, Danfeng Huang, Ke-Hu Wang, JunJiao Wang, Yulai Hu
{"title":"Synthesis of Fully Substituted Difluoromethylpyrazoles by Cyclization of Difluoroacetohydrazonoyl Bromides with 2-Acylacetonitriles or Malononitrile.","authors":"Si-Wei Wang, Jianzhong Zhang, Zhoubin Deng, Yuyu Lv, Danfeng Huang, Ke-Hu Wang, JunJiao Wang, Yulai Hu","doi":"10.1021/acs.joc.4c00828","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00828","url":null,"abstract":"<p><p>A concise and efficient method for the construction of fully substituted difluoromethylpyrazoles is achieved by a cyclization reaction between difluoroacetohydrazonoyl bromides and 2-acylacetonitrile or malononitrile. The method features advantages such as mild reaction conditions, broad substrate scope, good product yields, and high regioselectivity.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141589023","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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-Substituted 6-Azabicyclo[3.1.1]heptanes: Nonclassical Piperidine Isosteres for Drug Discovery. 3-取代的 6-氮杂双环[3.1.1]庚烷:用于药物发现的非经典哌啶异构体。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-07-11 DOI: 10.1021/acs.joc.4c00326
Anton V Chernykh, Bohdan V Vashchenko, Svitlana V Shishkina, Dmytro M Volochnyuk, Oleksandr O Grygorenko
{"title":"3-Substituted 6-Azabicyclo[3.1.1]heptanes: Nonclassical Piperidine Isosteres for Drug Discovery.","authors":"Anton V Chernykh, Bohdan V Vashchenko, Svitlana V Shishkina, Dmytro M Volochnyuk, Oleksandr O Grygorenko","doi":"10.1021/acs.joc.4c00326","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00326","url":null,"abstract":"<p><p>Advanced analogs of piperidine and smaller homologues of tropane─3-substituted 6-azabicyclo[3.1.1]heptanes─were synthesized on a large scale using readily available bulk reagents. The key step of the approach involved the double alkylation reaction of malonate with <i>cis</i>-2,4-bis(mesyloxymethyl)azetidine-1-carboxylate, in turn easily prepared on up to 1 kg scale. After hydrolysis, <i>N</i>-Boc-6-azabicyclo[3.1.1]heptane-3,3-dicarboxylic acid was obtained (up to 400 g in a single run), which was used as a common intermediate for the preparation of all the title building blocks. In particular, Pb(OAc)<sub>4</sub>-mediated oxidative decarboxylation of this intermediate gave 2,6-methanopiperidone derivative (up to 400 g scale), while monodecarboxylation gave <i>N</i>-Boc-6-azabicyclo[3.1.1]heptane-3-carboxylic acids as an easily separatable mixture of <i>cis</i> and <i>trans</i> diastereomers (up to 100 g scale). Further functional group transformations gave diastereopure <i>cis</i>- and <i>trans</i>-<i>N</i>-Boc-monoprotected diamines and amino alcohols. Molecular structure analysis using exit vector parameters (EVP) revealed that <i>cis</i> isomers of 3-substituted 6-azabicyclo[3.1.1]heptanes are three-dimensional analogs of common 1,4-disubstituted piperidine <i>chair</i> conformer, whereas <i>trans</i> isomers can be considered as unusual \"<i>boat</i>\" piperidines.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141578283","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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