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Organic catalysts and ligands derived from amino acids and peptides 源自氨基酸和肽的有机催化剂和配体
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-17 DOI: 10.1016/j.tet.2025.134671
Lipat Kaur , Karuna Thakare , Aman Singh Barahdia , Salil Pophali , Rajkumar Misra, Rahul Jain
{"title":"Organic catalysts and ligands derived from amino acids and peptides","authors":"Lipat Kaur ,&nbsp;Karuna Thakare ,&nbsp;Aman Singh Barahdia ,&nbsp;Salil Pophali ,&nbsp;Rajkumar Misra,&nbsp;Rahul Jain","doi":"10.1016/j.tet.2025.134671","DOIUrl":"10.1016/j.tet.2025.134671","url":null,"abstract":"<div><div>Amino acids and peptides have emerged as versatile organic catalysts and ligands owing to their unique structural diversity, biocompatibility, inherent chirality, and eco-friendly nature. Their applications span diverse fields, including asymmetric catalysis, metal complexation, and material science. The unique self-assembling properties of peptides are harnessed to create β-turn structures, foldamers, and nanotubes. The inherent chirality of amino acids and peptides is particularly valuable in asymmetric catalysis, enabling the development of highly stereoselective reactions crucial for pharmaceutical and fine chemical synthesis. Their ability to self-assemble into complex architectures also opens avenues for designing novel materials with tailored properties. Furthermore, the eco-friendly and biocompatible nature of these biomolecules aligns with the principles of green chemistry, making them ideal candidates for sustainable and environmentally benign processes. Synthetic amino acids and peptides hold tremendous promise as enzyme-like catalysts, capable of mimicking natural enzymatic systems to achieve remarkable catalytic efficiency and stereoselectivity. By leveraging the precise control over structure and functionality provided by synthetic modifications, researchers can create catalysts that rival or surpass traditional systems in performance. These advancements underline the potential of amino acids and peptides to revolutionize sustainable chemical processes, offering an innovative approach to addressing challenges in catalysis and material science. This review summarizes the advances in this domain, focusing on research published between 2018 and 2025 including selected amino acid examples from a broader body of research.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134671"},"PeriodicalIF":2.1,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847889","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Assembly of 3-halooxindoles via interrupted semipinacol Rearrangement: Enabling concise total synthesis of CPC-1 通过中断半匹纳酚重排组装3-卤代烷孔：使CPC-1的简洁全合成成为可能
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-16 DOI: 10.1016/j.tet.2025.134672
Yaoyao Liu , Yating Zhang , Fan Zhang, Mengqi Wang, Jun Xu
{"title":"Assembly of 3-halooxindoles via interrupted semipinacol Rearrangement: Enabling concise total synthesis of CPC-1","authors":"Yaoyao Liu ,&nbsp;Yating Zhang ,&nbsp;Fan Zhang,&nbsp;Mengqi Wang,&nbsp;Jun Xu","doi":"10.1016/j.tet.2025.134672","DOIUrl":"10.1016/j.tet.2025.134672","url":null,"abstract":"<div><div>In continuation of our research interest in oxidation of indoles, we further explore the direct oxidation of indoles to 3-halooxindoles promoted by the combination of NCS, H<sub>2</sub>O, and NaIO<sub>4</sub>, thereby suppressing the competitive semipinacol rearrangement reaction. This methodology was demonstrated to be a robust protocol mainly consisting of broad substrate scope and excellent functional compatibility, thus enabling the preparation of high added-value versatile building blocks susceptible to further functionalization. Additionally, synthesis of natural product CPC-1 from commercially available starting materials has also been achieved in four steps using this reaction as a key transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134672"},"PeriodicalIF":2.1,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Recent advances in skeletal construction strategies and late-stage functionalization in the synthesis of natural triterpenoids 天然三萜合成中骨架构建策略和后期功能化的最新进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-16 DOI: 10.1016/j.tet.2025.134666
Jiang-Li Huang, Kun Li, Tong-Ling Cha, Dashan Li, Wen-Jing Wang, Li-Dong Shao
{"title":"Recent advances in skeletal construction strategies and late-stage functionalization in the synthesis of natural triterpenoids","authors":"Jiang-Li Huang,&nbsp;Kun Li,&nbsp;Tong-Ling Cha,&nbsp;Dashan Li,&nbsp;Wen-Jing Wang,&nbsp;Li-Dong Shao","doi":"10.1016/j.tet.2025.134666","DOIUrl":"10.1016/j.tet.2025.134666","url":null,"abstract":"<div><div>Natural triterpenoids represent a prominent class of secondary metabolites widely distributed in terrestrial plants and marine organisms. Characterized by intricate polycyclic architectures, these compounds exhibit a diverse array of significant biological activities that have garnered sustained research interest in both organic synthesis and medicinal chemistry communities. The strategic implementation of skeletal construction and late-stage functionalization methodologies have emerged as cornerstones in natural product synthesis. These approaches are frequently coupled with high-efficiency chemical transformations, including but not limited to electrocyclic processes, cycloaddition reactions, polyene cyclization cascades, skeletal rearrangements, and late-stage C(sp<sup>3</sup>)-H oxidations. Such innovative strategies have not only facilitated the total syntheses of complex triterpenoid but also significantly advanced the development of triterpenoid chemistry. This comprehensive review systematically examines the methodological breakthroughs and synthetic applications of skeletal construction tactics and late-stage functionalization in triterpenoid synthesis over the past decade.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134666"},"PeriodicalIF":2.1,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143843387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 aza-Diels-Alder reaction between cyclic imine and aza-ortho-quinone methide precursor to access polycyclic-fused tetrahydroquinazoline 环亚胺与偶氮-邻醌甲酰前体间的偶氮- diols - alder反应制备多环熔合四氢喹啉
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-15 DOI: 10.1016/j.tet.2025.134665
Xiaoke Zhang , Lu He , Xuan Zhang , Mao Lin , Xiaojiang Huang , Lingjie Meng , Huawu Shao , Wei Jiao , Qianlu Xing
{"title":"The aza-Diels-Alder reaction between cyclic imine and aza-ortho-quinone methide precursor to access polycyclic-fused tetrahydroquinazoline","authors":"Xiaoke Zhang ,&nbsp;Lu He ,&nbsp;Xuan Zhang ,&nbsp;Mao Lin ,&nbsp;Xiaojiang Huang ,&nbsp;Lingjie Meng ,&nbsp;Huawu Shao ,&nbsp;Wei Jiao ,&nbsp;Qianlu Xing","doi":"10.1016/j.tet.2025.134665","DOIUrl":"10.1016/j.tet.2025.134665","url":null,"abstract":"<div><div>The aza-Diels-Alder reaction of cyclic imine with <em>N</em>-(<em>o</em>-chloromethyl) aryl amide has been developed. This method provides a highly efficient one-step strategy for constructing diverse ring-fused tetrahydroquinazoline scaffolds, including indolopyrido-tetrahydroquinazoline and isoquinolino-tetrahydroquinazoline derivatives, under mild conditions. The reactions achieved yields ranging from 47 % to 92 %.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134665"},"PeriodicalIF":2.1,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143867727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Supramolecular assembly-based tuning of optical properties of pyrrolidine, pyrimidine and morpholine functionalized naphthalimides 吡咯烷、嘧啶和啉功能化萘酰亚胺光学性质的超分子组装调谐
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-15 DOI: 10.1016/j.tet.2025.134655
Viral Khatri , Alisha Sengupta , Raj Dave , Rajesh Bhosale , Nidhi Gour , Deepak Asthana
{"title":"Supramolecular assembly-based tuning of optical properties of pyrrolidine, pyrimidine and morpholine functionalized naphthalimides","authors":"Viral Khatri ,&nbsp;Alisha Sengupta ,&nbsp;Raj Dave ,&nbsp;Rajesh Bhosale ,&nbsp;Nidhi Gour ,&nbsp;Deepak Asthana","doi":"10.1016/j.tet.2025.134655","DOIUrl":"10.1016/j.tet.2025.134655","url":null,"abstract":"<div><div>Fluorophores capable of exhibiting aggregation induced emission enhancement (AIEE) belong to an extremely important class of molecular materials. With the widespread application that ranges from medicinal usage to light emitting device fabrications, AIEE systems are known to offer a plethora of properties which has made them as one of the most heavily explored materials in the recent past. In the present work, we have prepared three naphthalimide derivatives that form self-assembled structures in DMSO/H<sub>2</sub>O mixtures and exhibit strong AIEE behavior. Steady-state and time-resolved fluorescence spectroscopic studies have been performed to explore the self-assembly process and its impact on the fluorescence and excited state lifetime.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134655"},"PeriodicalIF":2.1,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143843388","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Total synthesis of D-lyxo- and D-xylo-phytospingosines and fully acylated sphingofungin B D-lyxo-和d -xylo-植物旋光素和全酰化旋光素B的合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-12 DOI: 10.1016/j.tet.2025.134657
Gangarajulu Kesavulu, Kavirayani R. Prasad
{"title":"Total synthesis of D-lyxo- and D-xylo-phytospingosines and fully acylated sphingofungin B","authors":"Gangarajulu Kesavulu,&nbsp;Kavirayani R. Prasad","doi":"10.1016/j.tet.2025.134657","DOIUrl":"10.1016/j.tet.2025.134657","url":null,"abstract":"<div><div>A short synthetic sequence for the synthesis of D-<em>lyxo</em> and D-<em>xylo</em>-phytosphingosine and fully acylated sphingofungin B methyl ester is presented. The key reaction in the synthesis is the addition of lithio tris(methylthio)methane to sulfinimine to install the required chiral amino acid/amino alcohol component.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134657"},"PeriodicalIF":2.1,"publicationDate":"2025-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143834636","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Recent advances in directing group-free 1,2-dialkylation of alkenes 烯烃定向无基团1,2-二联化反应研究进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-11 DOI: 10.1016/j.tet.2025.134656
Yu-Qi Wang, Boon Chong Lee, Tong-De Tan, Ming Joo Koh
{"title":"Recent advances in directing group-free 1,2-dialkylation of alkenes","authors":"Yu-Qi Wang,&nbsp;Boon Chong Lee,&nbsp;Tong-De Tan,&nbsp;Ming Joo Koh","doi":"10.1016/j.tet.2025.134656","DOIUrl":"10.1016/j.tet.2025.134656","url":null,"abstract":"<div><div>The 1,2-dialkylation of alkenes is a valuable class of reactions in organic synthesis, enabling the formation of C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bonds that form the backbone of pharmaceuticals, materials, and natural products. This transformation offers a straightforward approach to construct complex molecular structures. Despite past advancements in chemistry, challenges such as regioselectivity control and β-hydride elimination still persist. In this review, we discuss recent progress in transition metal catalysis, photocatalysis and electrochemical methods for 1,2-dialkylation in the absence of directing auxiliaries, focusing on scope, mechanistic insights and potential for late-stage functionalization. We also address current limitations and suggest future directions in this area of research.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134656"},"PeriodicalIF":2.1,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143830429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Progress on ruthenium catalysts for efficiently promoting Z-selective olefin metathesis 高效促进z选择性烯烃反应的钌催化剂研究进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-10 DOI: 10.1016/j.tet.2025.134654
Shijie Bo , Ziying Xiong , Yaxin Wang , Hui Wang , Lin-Bao Zhang
{"title":"Progress on ruthenium catalysts for efficiently promoting Z-selective olefin metathesis","authors":"Shijie Bo ,&nbsp;Ziying Xiong ,&nbsp;Yaxin Wang ,&nbsp;Hui Wang ,&nbsp;Lin-Bao Zhang","doi":"10.1016/j.tet.2025.134654","DOIUrl":"10.1016/j.tet.2025.134654","url":null,"abstract":"<div><div>Olefin metathesis is a pivotal method for the synthesis of organic molecules and is widely applied in industrial production. Stereoselective olefin metathesis, as a method for selectively producing <em>E</em>-olefins and <em>Z</em>-olefins, has garnered considerable attention. This review article summarizes the reports on the use of ruthenium catalysts for <em>Z</em>-selective olefin metathesis reactions. Modifications of ruthenium catalyst ligands and control of reaction conditions have been employed to enhance the <em>Z</em>-selectivity in olefin metathesis. Ruthenium complexes containing adamantyl nitrate ligands, monothiol ligands, and dithiol ligands have demonstrated significant effects on the <em>Z</em>-selective metathesis of olefins. This clearly illustrates that ligand modification plays a crucial role in achieving stereospecific olefin metathesis reactions and offers insights for the design of future catalysts.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134654"},"PeriodicalIF":2.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143821064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-driven gem-difluorocyclopropanation of gem-difluoroalkenes with diazo compounds 可见光驱动宝石-二氟环丙烷与重氮化合物的合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-10 DOI: 10.1016/j.tet.2025.134653
Xinxin Han , Xin Liu , Christophe Len , Le Liu , Xin-Hua Duan , Mingyou Hu
{"title":"Visible-light-driven gem-difluorocyclopropanation of gem-difluoroalkenes with diazo compounds","authors":"Xinxin Han ,&nbsp;Xin Liu ,&nbsp;Christophe Len ,&nbsp;Le Liu ,&nbsp;Xin-Hua Duan ,&nbsp;Mingyou Hu","doi":"10.1016/j.tet.2025.134653","DOIUrl":"10.1016/j.tet.2025.134653","url":null,"abstract":"<div><div>A highly efficient approach is outlined for <em>gem</em>-difluorocyclopropanation of diazo compounds utilizing visible light catalysis. This method is distinguished by its mild reaction conditions, operational simplicity, broad substrate scope, excellent diastereoselectivity and exceptional synthetic efficacy. Notably, the synthesis of <em>gem</em>-difluorocyclopropanes is achieved without the necessity of transition metal catalysis or photocatalysts. In contrast to traditional methods of <em>gem</em>-difluorocyclopropane synthesis, this method allows for the direct synthesis of various sterically hindered <em>gem</em>-difluorocyclopropanes in a single step under mild conditions, while also demonstrating outstanding stereoselectivity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134653"},"PeriodicalIF":2.1,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143864480","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Ultrasound-enhanced A3 coupling: Ferrocene-infused ionic liquid on silica nanospheres for efficient Quinoline derivatives synthesis 超声增强的A3偶联：二氧化硅纳米球上注入二茂铁离子液体用于喹啉衍生物的高效合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-09 DOI: 10.1016/j.tet.2025.134633
Ahmad Sajjadi , Suranjana V. Mayani , Suhas Ballal , Shaker Al-Hasnaawei , Abhayveer Singh , Kattela Chennakesavulu , Kamal Kant Joshi
{"title":"Ultrasound-enhanced A3 coupling: Ferrocene-infused ionic liquid on silica nanospheres for efficient Quinoline derivatives synthesis","authors":"Ahmad Sajjadi ,&nbsp;Suranjana V. Mayani ,&nbsp;Suhas Ballal ,&nbsp;Shaker Al-Hasnaawei ,&nbsp;Abhayveer Singh ,&nbsp;Kattela Chennakesavulu ,&nbsp;Kamal Kant Joshi","doi":"10.1016/j.tet.2025.134633","DOIUrl":"10.1016/j.tet.2025.134633","url":null,"abstract":"<div><div>The synthesis of quinoline derivatives via A3 coupling has garnered significant attention due to the versatile applications of these compounds in pharmaceuticals and agrochemicals. This study presents an innovative approach utilizing ultrasound-enhanced A3 coupling facilitated by ferrocene-infused ionic liquid (FIL) supported on silica nanospheres (SiO<sub>2</sub>@Thiazol-Cl@Fc). The incorporation of ferrocene enhances the catalytic activity and promotes electron transfer processes, leading to improved reaction rates and yields. The ultrasound-assisted method further accelerates the reaction kinetics by providing localized energy, resulting in efficient mixing and enhanced mass transfer. Comprehensive optimization studies were conducted to evaluate the effects of various parameters, including catalyst loading, reaction temperature, and ultrasound intensity. Characterization of the synthesized silica nanospheres was performed using techniques such as scanning electron microscopy (SEM), Fourier-transform infrared spectroscopy (FTIR), and thermogravimetric analysis (TGA). The developed catalytic system demonstrated remarkable efficiency and selectivity for forming quinoline derivatives under mild reaction conditions. This work highlights the potential of combining ultrasound technology with novel catalytic systems for sustainable organic synthesis, paving the way for future advancements in green chemistry methodologies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134633"},"PeriodicalIF":2.1,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143877139","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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