Advanced Synthesis & Catalysis最新文献_第10页

DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols DMSO/SOCl2 介导的原炔醇硫代甲基萘合成反应

IF 4.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401025

Zhihua Wang , Wang‐Fu Liang , Xinglei He , Jingheng Li , Ke‐Yin Ye

引用次数: 0

Visible‐Light‐Induced Stereoselective C(sp3)−C(sp3)−H Glycosylation for the Synthesis of C‐Glycoamino Acid Derivatives 可见光诱导的立体选择性 C(sp3)-C(sp3)-H 糖基化合成 C-氨基乙酸衍生物

IF 4.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202400875

Guanghui Lv , Pingping Ruan , Hui Sun , Yafei Zhu , Mi Wang , Cuimei Zhang , Jian Chen , Li Guo , Yong Wu

{"title":"Visible‐Light‐Induced Stereoselective C(sp3)−C(sp3)−H Glycosylation for the Synthesis of C‐Glycoamino Acid Derivatives","authors":"Guanghui Lv , Pingping Ruan , Hui Sun , Yafei Zhu , Mi Wang , Cuimei Zhang , Jian Chen , Li Guo , Yong Wu","doi":"10.1002/adsc.202400875","DOIUrl":"10.1002/adsc.202400875","url":null,"abstract":"<div><div>Chiral C‐Glycosyl amino acids are prevalent structural motifs found in pharmaceuticals and natural products, making them a significant dimension for exploration in modern pharmaceutical and medicinal chemistry. However, the current synthesis methods for these compounds face numerous environmental and practical challenges, highlighting the critical need to establish more sustainable approaches. Herein, we report a simple and powerful strategy for the stereoselective synthesis of C‐glycoamino acids derivatives. This method features the design and use of (−)/(+)‐camphorsultam as an ideal chiral auxiliary, shielding one prochiral face of the glycine α‐carbon efficiently and imposing a high kinetic barrier for the epimerization of thus‐generated chiral α‐carbon that two configuration products of R and S could be achieved independently. It proceeds under mild conditions, shows broad scope, and allows for the direct stereoselective glycosylation without metal and chiral ligand.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202400875"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317227","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

Photocatalytic Silylation of Aryl Alkynoates: Synthesis of Silylated Coumarins 芳基炔酸盐的光催化硅烷化：硅烷化香豆素的合成

IF 4.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401007

Ravikumar Ladumor , Sourav Samanta , Sermadurai Selvakumar

引用次数: 0

Selective 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis 通过能量转移催化异硫氰酸酯的选择性 1,2-羧化反应获得 S-取代的异硫脲类化合物

IF 4.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401233

Li‐Ning Chen , Shu‐Nuo Liang , Juan Luo , Dan‐Na Chen , Zhi‐Peng Ye , Peng‐Ju Xia

引用次数: 0

Modular Chiral Bithiophene‐2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)‐Catalysed Friedel‐Crafts Alkylation 模块化手性噻吩-2NO 配体：不对称钯（II）催化的 Friedel-Crafts 烷基化反应中的合成与应用

IF 4.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401348

Xian‐Qiao Zhu , Wu‐Wu Li , Lin‐Lu Liu , Ke‐Lan Xu , Li‐Jun Peng , Min Zhang , Xiong‐Li Liu , Wen‐Jing Zhang

{"title":"Modular Chiral Bithiophene‐2NO Ligands: Synthesis and Application in Asymmetric Palladium(II)‐Catalysed Friedel‐Crafts Alkylation","authors":"Xian‐Qiao Zhu , Wu‐Wu Li , Lin‐Lu Liu , Ke‐Lan Xu , Li‐Jun Peng , Min Zhang , Xiong‐Li Liu , Wen‐Jing Zhang","doi":"10.1002/adsc.202401348","DOIUrl":"10.1002/adsc.202401348","url":null,"abstract":"<div><div>The development of privileged thiophene‐type ligand remains highly desirable, owing to the high coordination ability of sulfur atom to most of the soft metals. Herein, a new class of <em>C<sub>2</sub></em>‐symmetric rigid chiral tertiary amine‐derived dioxide ligands with a coordinating bithiophene bridge was developed in a convenient synthetic route with 25–62% overall yields. The bithiophene‐2NO‐palladium(II) catalyst system was generated <em>in situ</em> and found to be highly capable catalyst in the asymmetric Friedel‐Crafts alkylation of indoles. Excellent yields (up to 92%) and high enantioselectivities (up to >99% ee) are obtained for a wide range of substrates under mild conditions. Control experiments and DFT calculations revealed the origins of the enantioselectivity. This represented the first example of chiral thiophene ligands coordinating with soft metal Pd(II) in the asymmetric Friedel‐Crafts alkylation. Experiments revealed that the counteranion is involved in the stereoselectivity‐determining step in this soft palladium(II) catalysis, and the additional NO and thiophene in ligands can act as the second chelation site and thus reduce the amount of free metal ions for suppressing background reaction in the catalytic system.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401348"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142713064","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

Biomimetic Orthogonal Removal of Arylacyl Protecting Groups from the C-Terminus of Substituted Amino Acids and Oligopeptides via Flavin N(5)-iminium Covalent Adducts

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-03 DOI: 10.1002/adsc.202401556

Tetiana Pavlovska, Martin Havlik, Magdalena Labikova, Radek Cibulka

{"title":"Biomimetic Orthogonal Removal of Arylacyl Protecting Groups from the C-Terminus of Substituted Amino Acids and Oligopeptides via Flavin N(5)-iminium Covalent Adducts","authors":"Tetiana Pavlovska, Martin Havlik, Magdalena Labikova, Radek Cibulka","doi":"10.1002/adsc.202401556","DOIUrl":"https://doi.org/10.1002/adsc.202401556","url":null,"abstract":"Flavin co-factors and other flavin derivatives are traditionally associated with one- or two-electron redox reactions. Flavins also form covalent intermediates with a variety of substrates. While extensive attention has focused on reactions at the C(4a) position of the flavin ring, recent interest has shifted toward the dynamic potential of the N(5) atom. In our study, we demonstrate the formation of artificial flavin N(5)-iminium covalent adducts via nucleophilic attack by enolates derived from arylacyl esters at the flavin N(5) position. This interaction mimics the biosynthesis of ether phospholipids catalysed by alkyl-dihydroxyacetone phosphate synthase via an N(5)-FAD iminium adduct formation and fatty acid release. Accordingly, we developed a method for the selective removal of phenacyl and 2-naphthylacetyl protecting groups from the C-terminus of α-amino acids and di- and tripeptides using biomimetic flavin organocatalysis. Although many approaches are currently available for protection of C-terminus of peptides, their removal often requires harsh conditions, which cause racemization and the loss of optical purity, together with other side reactions. Our method is versatile, mild, orthogonal to most functional and protecting groups and maintains optical purity of α-amino acids. From general point of view, the method signifies the groundbreaking application of the non-canonical reactivity of flavins in organic synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"77 4 Pt 2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143083593","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

Rubottom Oxidation Reaction Inspired Divergent Synthesis of α-Hydroxy Amidines, α-Bromo Amidines and Tribrominated Indole Derivatives

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-03 DOI: 10.1002/adsc.202401356

Yan-Qiu Deng, Chang-Qing Qin, Hai Ren, Guoshu Chen, Chen-Chen Ni, Yun-Lin Liu

引用次数: 0

Metal‐free, Selective Ortho‐Deuteration of N‐heterocyclic Oxides

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-02-01 DOI: 10.1002/adsc.202401585

Arianna Montoli, Alessandro Dimasi, Andrea Citarella, Paolo Ronchi, Daniele Passarella, Valerio Fasano

引用次数: 0

Electrochemical umpolung of C‐H nucleophiles bearing three electron‐withdrawing groups to trigger radical 1,2‐alkylarylations of allylic alcohols 带有三个电子抽离基团的 C-H 亲核物的电化学umpolung 触发烯丙基醇的 1,2-烷基芳基自由基反应

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-01-31 DOI: 10.1002/adsc.202401522

Qibin Li, Die Hu, Kun Xu, Cheng-Chu Zeng

引用次数: 0

Photo-Induced 3-Alkylation of Coumarins with Alkyl halides

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401579

Cheng Yan, Wen-Jiao Zhang, Liu-Yan Qiu, Rui Wang, Weiguo Cao, Zhikun Zhang, Xiao-Jun Tang

引用次数: 0