The Ir III /Ni II metallaphotoredox-catalyzed enantioselective cross-coupling of chiral α-(hetero)aryl amines was systematically investigated using density functional theory (DFT) calculations. Both oxidative-quenching (Ir III -*Ir III -Ir IV -Ir III ) and reductivequenching (Ir III -*Ir III -Ir II -Ir III ) photoredox cycles were found to be compatible with the nickel catalytic cycle (Ni II -Ni I -Ni III -Ni II ).Mechanistic analysis indicates that the overall transformation proceeds through three fundamental steps: single-electron transfer, oxidative addition, and stepwise outer-sphere reductive elimination, with oxidative addition identified as the ratedetermining step. Notably, the enantio-determining C⎯C bond-forming event occurs via an ion-pair intermediate embedded within the outer-sphere reductive-elimination pathway. Furthermore, the high enantioselectivity of the process originates predominantly from steric interactions between the substrate and the chiral ligand. These insights clarify the mechanistic basis of this photoredox-mediated dual-catalytic asymmetric transformation and may guide the design of next-generation metallaphotoredox asymmetric methodologies.
采用密度泛函理论（DFT）对Ir /Ni金属光氧化还原催化手性α-（杂）芳基胺的对映选择性交叉偶联进行了系统研究。氧化猝灭（Ir III -*Ir III -Ir IV -Ir III）和还原性猝灭（Ir III -*Ir III -Ir II -Ir III）光氧化还原循环与镍催化循环（Ni II -Ni I -Ni III -Ni II）相容。机理分析表明，整个转化过程通过三个基本步骤进行：单电子转移、氧化加成和逐步外球还原消除，其中氧化加成被确定为速率决定步骤。值得注意的是，决定对映体的C - C键形成事件是通过嵌入在外球还原-消除途径中的离子对中间体发生的。此外，该工艺的高对映选择性主要源于底物与手性配体之间的空间相互作用。这些见解阐明了这种光氧化还原介导的双催化不对称转化的机制基础，并可能指导下一代金属光氧化还原不对称方法的设计。
{"title":"Outer-Sphere Reductive Elimination as the Enantio-Determining Step in Ir III /Ni II Metallaphotoredox-Catalyzed α-(Hetero)aryl Amination: A DFT Study","authors":"Yabin Jiang, Wei Guan, Yujie Liang","doi":"10.1039/d5qo01726b","DOIUrl":"https://doi.org/10.1039/d5qo01726b","url":null,"abstract":"The Ir III /Ni II metallaphotoredox-catalyzed enantioselective cross-coupling of chiral α-(hetero)aryl amines was systematically investigated using density functional theory (DFT) calculations. Both oxidative-quenching (Ir III -*Ir III -Ir IV -Ir III ) and reductivequenching (Ir III -*Ir III -Ir II -Ir III ) photoredox cycles were found to be compatible with the nickel catalytic cycle (Ni II -Ni I -Ni III -Ni II ).Mechanistic analysis indicates that the overall transformation proceeds through three fundamental steps: single-electron transfer, oxidative addition, and stepwise outer-sphere reductive elimination, with oxidative addition identified as the ratedetermining step. Notably, the enantio-determining C⎯C bond-forming event occurs via an ion-pair intermediate embedded within the outer-sphere reductive-elimination pathway. Furthermore, the high enantioselectivity of the process originates predominantly from steric interactions between the substrate and the chiral ligand. These insights clarify the mechanistic basis of this photoredox-mediated dual-catalytic asymmetric transformation and may guide the design of next-generation metallaphotoredox asymmetric methodologies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"92 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145962322","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}
Michel Große, Christopher Marco Leonhardt, Hermann A. Wegner
The integration of cyclooctene-derived motifs into larger molecular frameworks has emerged as a promising strategy to construct switchable molecules and materials that rely on conformational changes of the central eight-membered ring. In this work, we developed a facile synthetic route to access dinaphthocycloocta-1,5-dienes (DNCODs) relying on Lewis acid catalyzed inverse electron-demand Diels−Alder (IEDDA) reactions of phthalazines and cyclooct-1-en-5-yne derivatives. By employing two sequential IEDDA reactions, the modular annulation of different naphthalene units to the cyclooctadiene core was achieved. While the resulting DNCODs were found to adopt a chair conformation in the crystalline state, variable temperature (VT) NMR spectroscopy revealed a dynamic equilibrium in solution, with the twist-boat conformer being favoured. These findings offer new opportunities for engineering switchable cyclooctene-based structures and integrating them into functional materials.
{"title":"Modular Assembly of Conformationally Dynamic Dinaphthocycloocta-1,5-dienes","authors":"Michel Große, Christopher Marco Leonhardt, Hermann A. Wegner","doi":"10.1039/d5qo01621e","DOIUrl":"https://doi.org/10.1039/d5qo01621e","url":null,"abstract":"The integration of cyclooctene-derived motifs into larger molecular frameworks has emerged as a promising strategy to construct switchable molecules and materials that rely on conformational changes of the central eight-membered ring. In this work, we developed a facile synthetic route to access dinaphthocycloocta-1,5-dienes (DNCODs) relying on Lewis acid catalyzed inverse electron-demand Diels−Alder (IEDDA) reactions of phthalazines and cyclooct-1-en-5-yne derivatives. By employing two sequential IEDDA reactions, the modular annulation of different naphthalene units to the cyclooctadiene core was achieved. While the resulting DNCODs were found to adopt a chair conformation in the crystalline state, variable temperature (VT) NMR spectroscopy revealed a dynamic equilibrium in solution, with the twist-boat conformer being favoured. These findings offer new opportunities for engineering switchable cyclooctene-based structures and integrating them into functional materials.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"265 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145962321","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}
Li Wuwu, Hong-Xing Cen, Di-Cheng Pan, Lin-Lu Liu, Li-Jun Peng, Zi-Hong Hu, Xiong-Li Liu
Terpyridine-type ligands were renowned for their rich coordination with various metal ions. However, their high cost and tedious preparation methods limit their further application in asymmetric catalysis. Herein, we prepared diverse crab-shape C2-symmetric chiral terpyridine-tethered bisulidine ligands (abbreviated as Tpy-bisulidines), readily derived from optically pure sulfonylated 1,2-diphenylethylenediamine, in operationally simple one step and up to 57% yield. They were proven to be a class of efficient chiral ligands for Ni(II)-catalyzed asymmetric inverse-electron-demand Hetero-Diels-Alder reactions (HDA) between β,γ-unsaturated α-ketoesters and electron-rich alkenes, such as 2,3-dihydrofuran and enecarbamates, affording the products in excellent enantioselectivities. In addition to the HDA reaction, the in-situ-generated chiral Tpy-bisulidines/Ni(OTf)2 complex was also applied in the asymmetric Michael addition, Friedel-Crafts alkylation and Mukaiyama-Michael reactions, achieving high stereoselectivities. These findings demonstrate the promising potential of the Tpy-bisulidine ligand as a privileged ligand for diversity-oriented asymmetric catalysis.
{"title":"Crab-shape C2-symmetric chiral Tpy-bisulidine ligands: design, synthesis and application in diversity-oriented asymmetric catalysis","authors":"Li Wuwu, Hong-Xing Cen, Di-Cheng Pan, Lin-Lu Liu, Li-Jun Peng, Zi-Hong Hu, Xiong-Li Liu","doi":"10.1039/d5qo01530h","DOIUrl":"https://doi.org/10.1039/d5qo01530h","url":null,"abstract":"Terpyridine-type ligands were renowned for their rich coordination with various metal ions. However, their high cost and tedious preparation methods limit their further application in asymmetric catalysis. Herein, we prepared diverse crab-shape C2-symmetric chiral terpyridine-tethered bisulidine ligands (abbreviated as Tpy-bisulidines), readily derived from optically pure sulfonylated 1,2-diphenylethylenediamine, in operationally simple one step and up to 57% yield. They were proven to be a class of efficient chiral ligands for Ni(II)-catalyzed asymmetric inverse-electron-demand Hetero-Diels-Alder reactions (HDA) between β,γ-unsaturated α-ketoesters and electron-rich alkenes, such as 2,3-dihydrofuran and enecarbamates, affording the products in excellent enantioselectivities. In addition to the HDA reaction, the in-situ-generated chiral Tpy-bisulidines/Ni(OTf)2 complex was also applied in the asymmetric Michael addition, Friedel-Crafts alkylation and Mukaiyama-Michael reactions, achieving high stereoselectivities. These findings demonstrate the promising potential of the Tpy-bisulidine ligand as a privileged ligand for diversity-oriented asymmetric catalysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145956250","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}
Wen-Bin Xu, Li-Na Yang, Yang-Shuang Wang, Yu Zhang, Xiao-Han Qiu, Yu-Ning Gao, Ming Bian, Cun-Feng Song, Hui-Yu Chen, Zhen-Jiang Liu
A Lewis acid-catalyzed cascade reaction has been developed for the synthesis of 2-alkenylaniline derivatives bearing an enone moiety. This method utilizes readily available N-aryl hydroxylamines and propargylic alcohols under mild conditions. The mechanism likely involves an intercepted Meyer-Schuster O-allenylation via SN1' reaction, followed by a [3,3]sigmatropic rearrangement/rearomatization sequence. When PMHS is introduced as a reducing agent, the enone intermediates undergo in situ reduction, followed by cyclization and elimination, enabling a one-pot synthesis of polysubstituted indoles. The reaction demonstrates broad functional group tolerance and offers a practical route to a wide range of multifunctionalized anilines, enones, and indoles in good yields.
采用Lewis酸催化级联反应合成了2-烯酮基苯胺衍生物。该方法在温和条件下利用易于获得的n -芳基羟胺和丙炔醇。其机制可能涉及通过SN1′反应截获的Meyer-Schuster o -烯化，随后是[3,3]异位重排/重芳构化序列。当PMHS作为还原剂引入时，烯酮中间体进行原位还原，然后进行环化和消除，从而可以一锅合成多取代吲哚。该反应显示了广泛的官能团耐受性，并提供了一个实用的途径，以良好的收率得到广泛的多功能化苯胺、烯酮和吲哚。
{"title":"Lewis acid-catalyzed cascade via intercepted Meyer-Schuster O-allenylation and [3,3]-sigmatropic rearrangement: Divergent synthesis of 2-alkenylanilines and indoles","authors":"Wen-Bin Xu, Li-Na Yang, Yang-Shuang Wang, Yu Zhang, Xiao-Han Qiu, Yu-Ning Gao, Ming Bian, Cun-Feng Song, Hui-Yu Chen, Zhen-Jiang Liu","doi":"10.1039/d5qo01615k","DOIUrl":"https://doi.org/10.1039/d5qo01615k","url":null,"abstract":"A Lewis acid-catalyzed cascade reaction has been developed for the synthesis of 2-alkenylaniline derivatives bearing an enone moiety. This method utilizes readily available N-aryl hydroxylamines and propargylic alcohols under mild conditions. The mechanism likely involves an intercepted Meyer-Schuster O-allenylation via SN1' reaction, followed by a [3,3]sigmatropic rearrangement/rearomatization sequence. When PMHS is introduced as a reducing agent, the enone intermediates undergo in situ reduction, followed by cyclization and elimination, enabling a one-pot synthesis of polysubstituted indoles. The reaction demonstrates broad functional group tolerance and offers a practical route to a wide range of multifunctionalized anilines, enones, and indoles in good yields.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145968886","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}
We report a mild three-component reaction system combining styrenes, alkenylboronic esters, and 4-cyanopyridine for the efficient synthesis of alkenes. Furthermore, we demonstrate the practical utility of this methodology through its application in the synthesis of 1,1-diarylalkanes using alkylboronic esters and its scalability and compatibility with late-stage functionalization of pharmaceutical molecules.
{"title":"Benzophenone-catalyzed alkenylative pyridylation of vinylarenes with alkenylboronic esters","authors":"Yuhui Ying, Zixiang Li, Bin Liu","doi":"10.1039/d5qo01578b","DOIUrl":"https://doi.org/10.1039/d5qo01578b","url":null,"abstract":"We report a mild three-component reaction system combining styrenes, alkenylboronic esters, and 4-cyanopyridine for the efficient synthesis of alkenes. Furthermore, we demonstrate the practical utility of this methodology through its application in the synthesis of 1,1-diarylalkanes using alkylboronic esters and its scalability and compatibility with late-stage functionalization of pharmaceutical molecules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145956256","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}
In this study, we report a DMSO/Tf2O-promoted regio- and Z-stereoselective sulfonyl functionalization of terminal alkynes that delivers diverse functionalized vinyl sulfones in a highly selective manner under tunable basic conditions. A variety of terminal alkynes, sodium sulfinates, and alkyl alcohols, (thiol)phenols, and selenophenol are viable in this transformation. Notably, the synthetic utility of this method is demonstrated by its applicability in scale-up reactions and efficient late-stage modification of target products and bioactive molecules.
{"title":"DMSO/Tf2O-promoted regio- and Z-stereoselective sulfonyl functionalization of terminal alkynes","authors":"Yuxin Guo, Hanru Tang, Zhiyan Liu, Zhiping Wang, Long-Yong Xie, Jian Wen","doi":"10.1039/d5qo01607j","DOIUrl":"https://doi.org/10.1039/d5qo01607j","url":null,"abstract":"In this study, we report a DMSO/Tf<small><sub>2</sub></small>O-promoted regio- and <em>Z</em>-stereoselective sulfonyl functionalization of terminal alkynes that delivers diverse functionalized vinyl sulfones in a highly selective manner under tunable basic conditions. A variety of terminal alkynes, sodium sulfinates, and alkyl alcohols, (thiol)phenols, and selenophenol are viable in this transformation. Notably, the synthetic utility of this method is demonstrated by its applicability in scale-up reactions and efficient late-stage modification of target products and bioactive molecules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145956247","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}
A metal- and additive-free ipso-benzylation of arylsilanes was developed to efficiently synthesize symmetrical and unsymmetrical diarylmethanes. In this process, hexafluoroisopropanol (HFIP) plays a dual role as a solvent and an activator of benzyl fluorides. Furthermore, the recyclability and reusability of the HFIP solvent make the reaction environmentally friendly. The protocol distinguishes its exclusive regioselectivity, mild reaction conditions, simplicity, and high efficiency. Additionally, this method also shows good compatibility in the preparation of propargyl arenes.
{"title":"Metal- and additive-free ipso-benzylation of arylsilanes to access diarylmethanes","authors":"Wanting Fu, Jialong Zhong, Shuang Lv, Xinyu Song, Yilin Xing, Zikun Wang","doi":"10.1039/d5qo01554e","DOIUrl":"https://doi.org/10.1039/d5qo01554e","url":null,"abstract":"A metal- and additive-free ipso-benzylation of arylsilanes was developed to efficiently synthesize symmetrical and unsymmetrical diarylmethanes. In this process, hexafluoroisopropanol (HFIP) plays a dual role as a solvent and an activator of benzyl fluorides. Furthermore, the recyclability and reusability of the HFIP solvent make the reaction environmentally friendly. The protocol distinguishes its exclusive regioselectivity, mild reaction conditions, simplicity, and high efficiency. Additionally, this method also shows good compatibility in the preparation of propargyl arenes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"50 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145956251","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}
Asymmetric sp³-sp³ cross-coupling reactions (including Csp³-Csp³, Csp³-Xsp3 and Xsp³-Xsp3 couplings) represent one of the most modular and straightforward methods to rapidly build saturation with control of stereochemistry by simply connecting two saturated coupling partners. However, asymmetric sp³-sp³ cross-couplingsstill remain challenging due to the increased steric hindrance and flexibility of coupling partners and intermediates, leading to enhanced competitive side reactions and increased difficulties in sp³-sp³ cross-couplings as well as enantioselectivity control. Over the past decades, earth-abundant transition-metal-catalysed redox-neutral cross-coupling between nucleophiles and electrophiles andreductive cross-coupling between two electrophiles have been developed for building stereogenic centers by sp³-sp³ coupling. In these two reaction modes, stoichiometric electrophiles required. On the other hand, asymmetric oxidative sp³-sp³ cross-coupling between two nucleophiles offers another alternative to access stereogenic centers by asymmetric sp³-sp³ cross-coupling. This reaction circumvents the use of electrophiles. Over past years, earth-abundant metal (e.g., Fe, Co, Ni, Cu)-catalysed asymmetric oxidative sp³-sp³ coupling reactions have achieved great progress for the efficient construction of chiral saturated C-C/X bonds. Thus, this review systematically summarizes research progress on this reaction mode with an emphasis on reaction development, mechanistic investigations, and synthetic applications of different catalytic systems. Moreover, perspectives on future development and key issues to be addressed are also discussed to provide further guidance for this area.
{"title":"Recent advances in earth-abundant transition-metal-catalysed asymmetric oxidative sp³-sp³ cross-couplings","authors":"Jiao He, Perla Bharath Kumar, Yu-Long Li, Qiong Yu, Wei Shu","doi":"10.1039/d5qo01749a","DOIUrl":"https://doi.org/10.1039/d5qo01749a","url":null,"abstract":"Asymmetric sp³-sp³ cross-coupling reactions (including Csp³-Csp³, Csp³-Xsp3 and Xsp³-Xsp3 couplings) represent one of the most modular and straightforward methods to rapidly build saturation with control of stereochemistry by simply connecting two saturated coupling partners. However, asymmetric sp³-sp³ cross-couplingsstill remain challenging due to the increased steric hindrance and flexibility of coupling partners and intermediates, leading to enhanced competitive side reactions and increased difficulties in sp³-sp³ cross-couplings as well as enantioselectivity control. Over the past decades, earth-abundant transition-metal-catalysed redox-neutral cross-coupling between nucleophiles and electrophiles andreductive cross-coupling between two electrophiles have been developed for building stereogenic centers by sp³-sp³ coupling. In these two reaction modes, stoichiometric electrophiles required. On the other hand, asymmetric oxidative sp³-sp³ cross-coupling between two nucleophiles offers another alternative to access stereogenic centers by asymmetric sp³-sp³ cross-coupling. This reaction circumvents the use of electrophiles. Over past years, earth-abundant metal (e.g., Fe, Co, Ni, Cu)-catalysed asymmetric oxidative sp³-sp³ coupling reactions have achieved great progress for the efficient construction of chiral saturated C-C/X bonds. Thus, this review systematically summarizes research progress on this reaction mode with an emphasis on reaction development, mechanistic investigations, and synthetic applications of different catalytic systems. Moreover, perspectives on future development and key issues to be addressed are also discussed to provide further guidance for this area.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145947490","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}
Zhuang Wang, Zhaoyu Zhang, Xinyu Xie, Song Qin, Shaomin Fu, Bo Liu
We herein report the synthetic efforts toward the tricyclic core of rhamnofolane-type diterpenoids, featuring a 5-exo/ring-expansion/6-exo radical cascade sequence. Furthermore, direct stereoselective editing of a sterically hindered allylic C–H bond enables the otherwise challenging conversion of cis-fused systems to their trans-fused analogs, providing a versatile platform for accessing this natural product family.
{"title":"Construction of the Tricyclic Core of Rhamnofolane-type Diterpenoids","authors":"Zhuang Wang, Zhaoyu Zhang, Xinyu Xie, Song Qin, Shaomin Fu, Bo Liu","doi":"10.1039/d5qo01699a","DOIUrl":"https://doi.org/10.1039/d5qo01699a","url":null,"abstract":"We herein report the synthetic efforts toward the tricyclic core of rhamnofolane-type diterpenoids, featuring a 5-exo/ring-expansion/6-exo radical cascade sequence. Furthermore, direct stereoselective editing of a sterically hindered allylic C–H bond enables the otherwise challenging conversion of cis-fused systems to their trans-fused analogs, providing a versatile platform for accessing this natural product family.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"129 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145947553","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}
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