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Highly Shielded Peroxo-Cerium(IV)-Containing Polyoxometalate: Synthesis, Structure, and Oxidative Studies 高屏蔽过氧化物铈(IV)-含多金属氧酸盐：合成、结构和氧化研究
ChemistryEurope Pub Date : 2025-06-03 DOI: 10.1002/ceur.202500082
Anusree Sundar, Danica Bajuk-Bogdanović, Gordana Ćirić-Marjanović, Talha Nisar, Veit Wagner, Arnulf Materny, Geoffrey B. Jameson, Bassem S. Bassil, Ulrich Kortz
{"title":"Highly Shielded Peroxo-Cerium(IV)-Containing Polyoxometalate: Synthesis, Structure, and Oxidative Studies","authors":"Anusree Sundar,&nbsp;Danica Bajuk-Bogdanović,&nbsp;Gordana Ćirić-Marjanović,&nbsp;Talha Nisar,&nbsp;Veit Wagner,&nbsp;Arnulf Materny,&nbsp;Geoffrey B. Jameson,&nbsp;Bassem S. Bassil,&nbsp;Ulrich Kortz","doi":"10.1002/ceur.202500082","DOIUrl":"10.1002/ceur.202500082","url":null,"abstract":"<p>The peroxo-bridged di-cerium(IV)-di-lithium-containing polyoxometalate [(Ce<sup>IV</sup><sub>2</sub>O<sub>2</sub>)Li<sub>2</sub>(P<sub>2</sub>W<sub>16</sub>O<sub>59</sub>)<sub>2</sub>]<sup>16−</sup> (<b>Ce</b><sub><b>2</b></sub><b>Li</b><sub><b>2</b></sub><b>P</b><sub><b>4</b></sub><b>W</b><sub><b>32</b></sub>) is synthesized in a one-pot aqueous synthetic procedure and isolated as a hydrated mixed alkali salt, K<sub>13.6</sub>Na<sub>1.4</sub>Li[(Ce<sup>IV</sup><sub>2</sub>O<sub>2</sub>)Li<sub>2</sub>(P<sub>2</sub>W<sub>16</sub>O<sub>59</sub>)<sub>2</sub>]·32H<sub>2</sub>O (<b>KNaLi-Ce</b><sub><b>2</b></sub><b>Li</b><sub><b>2</b></sub><b>P</b><sub><b>4</b></sub><b>W</b><sub><b>32</b></sub>). The novel polyanion <b>Ce</b><sub><b>2</b></sub><b>Li</b><sub><b>2</b></sub><b>P</b><sub><b>4</b></sub><b>W</b><sub><b>32</b></sub> comprises a side-on peroxo-group bridging two cerium(IV) and two lithium ions, which are encapsulated between two dilacunary, face-on {P<sub>2</sub>W<sub>16</sub>} Wells–Dawson units, with a vacant site in each of the two belts. The polyanion <b>Ce</b><sub><b>2</b></sub><b>Li</b><sub><b>2</b></sub><b>P</b><sub><b>4</b></sub><b>W</b><sub><b>32</b></sub> is characterized in the solid state by single-crystal X-ray diffraction, Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray photoelectron spectroscopy, and Raman spectroscopy and in solution by <sup>31</sup>P NMR and Raman spectroscopy, respectively. <b>Ce</b><sub><b>2</b></sub><b>Li</b><sub><b>2</b></sub><b>P</b><sub><b>4</b></sub><b>W</b><sub><b>32</b></sub> and the peroxo-group are shown to be highly stable in a large pH range and up to almost boiling temperatures, but at the same time the polyanion is reactive toward oxidation of triphenylphosphine, involving the peroxo group and the cerium(IV) centers.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500082","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144635551","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Construction of Hollow H-CuS/NiS2@CuS S-Scheme Heterostructure Photocatalyst with an Excellent Hydrogen Evolution Performance 具有优异析氢性能的空心h - cu /NiS2@CuS s型异质结构光催化剂的构建
ChemistryEurope Pub Date : 2025-05-30 DOI: 10.1002/ceur.202500073
Tao Zhou, Junzi Li, Xu Han, Yingyu Song, Menglong Liu, Jialiang Liu, Wen-Wen He, Thamraa AlShahrani, Shengqian Ma
{"title":"Construction of Hollow H-CuS/NiS2@CuS S-Scheme Heterostructure Photocatalyst with an Excellent Hydrogen Evolution Performance","authors":"Tao Zhou,&nbsp;Junzi Li,&nbsp;Xu Han,&nbsp;Yingyu Song,&nbsp;Menglong Liu,&nbsp;Jialiang Liu,&nbsp;Wen-Wen He,&nbsp;Thamraa AlShahrani,&nbsp;Shengqian Ma","doi":"10.1002/ceur.202500073","DOIUrl":"10.1002/ceur.202500073","url":null,"abstract":"<p>Heterojunction engineering is regarded as one of the most efficacious means to enhance the hydrogen evolution performance of photocatalysts. In this research, bimetal MOF-74 is grown on hollow Cu<sub>7</sub>S<sub>4</sub>, and after vulcanization, H-CuS/NiS<sub>2</sub>@CuS is obtained to form heterostructures. The experimental results indicate that the synthesized H-CuS/NiS<sub>2</sub>@CuS has an outstanding photocatalytic hydrogen evolution rate of 17.66 mmol g<sup>−1</sup> h<sup>−1</sup>, and its photocatalytic hydrogen evolution performance is much higher than that of single transition metal sulfide. Within the S-scheme heterojunction, the interfacial electric field causes a significant accumulation of photoelectrons on the conduction band of NiS<sub>2</sub>. Thus, it can maintain a high reducing property in the hydrogen evolution reaction and remarkably boosts the separation efficiency of photoelectrons and holes. This research offers a feasible scheme for the synthesis of highly efficient heterojunction photocatalysts.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500073","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144635673","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif 双环吡萘醌类天然产物的合成研究：二恶双环[3.3.1]壬烯基序的构建
ChemistryEurope Pub Date : 2025-05-29 DOI: 10.1002/ceur.202500086
Yoshio Ando, Sota Ajima, Ken Ohmori
{"title":"Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif","authors":"Yoshio Ando,&nbsp;Sota Ajima,&nbsp;Ken Ohmori","doi":"10.1002/ceur.202500086","DOIUrl":"10.1002/ceur.202500086","url":null,"abstract":"<p>A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid-type pyranonaphthoquinone-class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500086","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144635665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds 氢键中CH和OH作为质子供体的比较
ChemistryEurope Pub Date : 2025-05-28 DOI: 10.1002/ceur.202500088
Savannah Rawlings, Steve Scheiner
{"title":"Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds","authors":"Savannah Rawlings,&nbsp;Steve Scheiner","doi":"10.1002/ceur.202500088","DOIUrl":"10.1002/ceur.202500088","url":null,"abstract":"<p>The ability of the CH group to act as proton donor is now widely accepted, even if the H bonds (HBs), which it forms are typically much weaker than those of the hydroxyl group, particularly for a sp<sup>3</sup>-hybridized C. An NH<sub>3</sub> nucleophile is allowed to approach both the terminal methyl group and the hydroxyl of n-butanol, so as to form either a CH··N or OH··N HB. Density functional theory calculations show that the latter is much stronger than the former. However, the strength of the CH··N HB can be amplified and approach much closer to that of OH··N by appropriate placement of suitable electron-withdrawing and donating substituents on the butanol. The interaction energy of the CH··N HB reaches above 6–8 kcal mol<sup>−1</sup> in several cases, considerably larger than the prototype HB within the water dimer.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500088","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144634989","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ligand-Dependent Chemoselectivity in Gold-Catalyzed Reactions between Anthranils and Diynamides. Formation of Spiro Azacyclic Compounds versus 1-Imino-1H-Indene-3-Carboximidamides 金催化的邻蒽醌与双酰胺反应中配体依赖的化学选择性。螺旋氮杂环化合物与1-亚胺- 1h -茚-3-碳胺酰胺的形成
ChemistryEurope Pub Date : 2025-05-24 DOI: 10.1002/ceur.202500068
Satish Bhausaheb Dawange, Rai-Shung Liu
{"title":"Ligand-Dependent Chemoselectivity in Gold-Catalyzed Reactions between Anthranils and Diynamides. Formation of Spiro Azacyclic Compounds versus 1-Imino-1H-Indene-3-Carboximidamides","authors":"Satish Bhausaheb Dawange,&nbsp;Rai-Shung Liu","doi":"10.1002/ceur.202500068","DOIUrl":"10.1002/ceur.202500068","url":null,"abstract":"<p>Gold-catalyzed reactions between anthranils and diynamides have been investigated, and their reaction chemoselectivity relies on the types of gold catalysts. With the same anthranil/diynamide mixtures, the use of PPh<sub>3</sub>AuCl/AgNTf<sub>2</sub> leads to formation of spiro azacyclic compounds, whereas P(<i>t</i>-Bu)<sub>2</sub>(<i>o</i>-biphenyl)AuCl/AgNTf<sub>2</sub> preferably yields 1-imino-1<i>H</i>-indene-3-carboximidamides instead. In the PPh<sub>3</sub>AuCl/AgNTf<sub>2</sub> system, an indole intermediate at low temperature for X-ray diffraction study is isolated; this isolable indole species requires anthranil and gold catalyst for efficient formation of spiro azacyclic products. In the case of P(<i>t</i>-Bu)<sub>2</sub>(<i>o</i>-biphenyl)AuCl/AgNTf<sub>2</sub>, the mechanism of its resulting 1-imino-1<i>H</i>-indene-3-carboximidamides is postulated based on literature reports.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500068","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144635650","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene 二茂铁磷离子对烯类化合物的活化作用：一种惠兰二茂铁中间体的分离
ChemistryEurope Pub Date : 2025-05-23 DOI: 10.1002/ceur.202500031
Corina Stoian, Carolin Exner, Pim Puylaert, Moritz Hornig, Serhiy Demeshko, Malte Fischer, Emanuel Hupf, Jens Beckmann
{"title":"Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene","authors":"Corina Stoian,&nbsp;Carolin Exner,&nbsp;Pim Puylaert,&nbsp;Moritz Hornig,&nbsp;Serhiy Demeshko,&nbsp;Malte Fischer,&nbsp;Emanuel Hupf,&nbsp;Jens Beckmann","doi":"10.1002/ceur.202500031","DOIUrl":"https://doi.org/10.1002/ceur.202500031","url":null,"abstract":"<p>The reaction of the diferrocenylphosphenium ion with four terminal allenes follows two different pathways, via allyl or vinyl carbocations, which proceed with electrophilic substitution reactions at one ferrocenyl moiety to form persistent Wheland intermediates and eventually alkenyldiferrocenylphosphonium salts. The reaction of the diferrocenylphosphenium ion with 2-(trimethylsilyl)-2,3-pentadiene affords a stable Wheland intermediate of ferrocene in high yields, which is isolated and fully characterized.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500031","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145129227","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Exploring the Reactivity of Germole Dianions with Aluminum Trichloride: Uncovering Versatile Pathways 探索德国钠离子与三氯化铝的反应性：揭示多种途径
ChemistryEurope Pub Date : 2025-05-23 DOI: 10.1002/ceur.202500081
Lena Albers, Marc Schmidtmann, Thomas Müller
{"title":"Exploring the Reactivity of Germole Dianions with Aluminum Trichloride: Uncovering Versatile Pathways","authors":"Lena Albers,&nbsp;Marc Schmidtmann,&nbsp;Thomas Müller","doi":"10.1002/ceur.202500081","DOIUrl":"10.1002/ceur.202500081","url":null,"abstract":"<p>The reactivity analysis of dipotassiumgermoldiides K<sub>2</sub><b>[1]</b> with aluminum trichloride in the presence of donors uncovers an unexpectedly broad range of products. The specific product formed varies, based on the donor's characteristics, its size, and the stoichiometric ratio between the donor and the aluminium trichloride. This leads to the formation of various products, including alumole complexes of germanium <b>3(Do)</b> (with Do = OEt<sub>2</sub>, <sup><i>i</i>Pr2Me2</sup>Im), cationic germole complexes of aluminylenes [<b>14</b>]<sup>+</sup>, and 2<i>H</i>-germole derivatives such as <b>15a</b>. The alumole complexes of germanium <b>3</b> are structurally best described as <i>nido</i>-type clusters or aluminagerma[5]pyramidanes. They show significant Lewis acidity and can be isolated only in the form of their donor complexes <b>3</b>(<b>Do</b>). The 2<i>H</i>-germole derivative <b>15a</b> promises a high synthetic potential due to its unprecedented germenide (R<sub>2</sub>C = Ge(:)-R) group group, which is part of a butadiene system and substituted with a reactive C–Al functionality.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500081","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144635619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene 二茂铁磷离子对烯类化合物的活化作用：一种惠兰二茂铁中间体的分离
ChemistryEurope Pub Date : 2025-05-23 DOI: 10.1002/ceur.202500031
Corina Stoian, Carolin Exner, Pim Puylaert, Moritz Hornig, Serhiy Demeshko, Malte Fischer, Emanuel Hupf, Jens Beckmann
{"title":"Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene","authors":"Corina Stoian,&nbsp;Carolin Exner,&nbsp;Pim Puylaert,&nbsp;Moritz Hornig,&nbsp;Serhiy Demeshko,&nbsp;Malte Fischer,&nbsp;Emanuel Hupf,&nbsp;Jens Beckmann","doi":"10.1002/ceur.202500031","DOIUrl":"https://doi.org/10.1002/ceur.202500031","url":null,"abstract":"<p>The reaction of the diferrocenylphosphenium ion with four terminal allenes follows two different pathways, via allyl or vinyl carbocations, which proceed with electrophilic substitution reactions at one ferrocenyl moiety to form persistent Wheland intermediates and eventually alkenyldiferrocenylphosphonium salts. The reaction of the diferrocenylphosphenium ion with 2-(trimethylsilyl)-2,3-pentadiene affords a stable Wheland intermediate of ferrocene in high yields, which is isolated and fully characterized.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500031","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145129292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Indole Synthesis via Allenyl Ester; Enantioselective Total Synthesis of Geissoschizoline 烯丙基酯合成吲哚的研究盖索schizoline的对映选择性全合成
ChemistryEurope Pub Date : 2025-05-19 DOI: 10.1002/ceur.202500129
Sohsuke Moriue, Honami Nishioka, Yuto Fukuda, Hiromitsu Takayama, Mariko Kitajima, Hayato Ishikawa
{"title":"Indole Synthesis via Allenyl Ester; Enantioselective Total Synthesis of Geissoschizoline","authors":"Sohsuke Moriue,&nbsp;Honami Nishioka,&nbsp;Yuto Fukuda,&nbsp;Hiromitsu Takayama,&nbsp;Mariko Kitajima,&nbsp;Hayato Ishikawa","doi":"10.1002/ceur.202500129","DOIUrl":"https://doi.org/10.1002/ceur.202500129","url":null,"abstract":"<p>Methyl indole-2-acetate is a key structural motif in plant-derived indole alkaloids. In this study, a mild and efficient protocol is presented for its preparation using readily available aniline derivatives, which are synthesized from malonic esters. The reaction proceeds via an allenyl ester intermediate, with NaCN-mediated indole formation occurring at ambient temperature, affording high yields and broad substrate scope. The synthetic utility of this approach is demonstrated through the asymmetric total synthesis of geissoschizoline, a <i>Strychnos</i>-type monoterpenoid indole alkaloid. This synthesis not only establishes a novel route to monoterpenoid indole alkaloids but also achieves complete stereochemical control in constructing the six chiral centers of the natural product.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500129","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145129171","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Indole Synthesis via Allenyl Ester; Enantioselective Total Synthesis of Geissoschizoline 烯丙基酯合成吲哚的研究盖索schizoline的对映选择性全合成
ChemistryEurope Pub Date : 2025-05-19 DOI: 10.1002/ceur.202500129
Sohsuke Moriue, Honami Nishioka, Yuto Fukuda, Hiromitsu Takayama, Mariko Kitajima, Hayato Ishikawa
{"title":"Indole Synthesis via Allenyl Ester; Enantioselective Total Synthesis of Geissoschizoline","authors":"Sohsuke Moriue,&nbsp;Honami Nishioka,&nbsp;Yuto Fukuda,&nbsp;Hiromitsu Takayama,&nbsp;Mariko Kitajima,&nbsp;Hayato Ishikawa","doi":"10.1002/ceur.202500129","DOIUrl":"https://doi.org/10.1002/ceur.202500129","url":null,"abstract":"<p>Methyl indole-2-acetate is a key structural motif in plant-derived indole alkaloids. In this study, a mild and efficient protocol is presented for its preparation using readily available aniline derivatives, which are synthesized from malonic esters. The reaction proceeds via an allenyl ester intermediate, with NaCN-mediated indole formation occurring at ambient temperature, affording high yields and broad substrate scope. The synthetic utility of this approach is demonstrated through the asymmetric total synthesis of geissoschizoline, a <i>Strychnos</i>-type monoterpenoid indole alkaloid. This synthesis not only establishes a novel route to monoterpenoid indole alkaloids but also achieves complete stereochemical control in constructing the six chiral centers of the natural product.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500129","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145129165","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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