Synlett最新文献

英文中文

Chiral-Bisphosphine-Catalyzed Asymmetric Staudinger/Aza-Wittig Reaction: Development, Mechanism Study, and Synthetic Application 手性双膦催化的不对称施陶丁格/阿扎-维蒂希反应：开发、机理研究和合成应用

IF 2 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-08-22 DOI: 10.1055/s-0043-1775038

Hongzhi Yang, Truc Quynh Nguyen, Yefeng Tang

The enantioselective desymmetrization of 2,2-disubstituted cyclohexane-1,3-diones has been realized through an unprecedented chiral-bisphosphine-catalyzed asymmetric Staudinger/aza-Wittig reaction. The key to this work’s success lies in utilizing an electronically rich and sterically hindered chiral bisphosphine reagent, namely DuanPhos, as a catalyst. In addition, a unique reductive system was established to address the requisite P^III/PV = O redox cycle. The mechanism of the chiral-bisphosphine-catalyzed asymmetric Staudinger/aza-Wittig reaction has been elucidated through combined computational and experimental studies. Several crinine-type amaryllidaceae alkaloids have been synthesized concisely, hinging on the newly developed methodology.

通过前所未有的手性双膦催化不对称施陶丁格/扎-维蒂希反应，实现了 2,2-二取代环己烷-1,3-二酮的对映选择性去对称化。这项工作取得成功的关键在于利用了一种电子丰富、立体受阻的手性双膦试剂（即 DuanPhos）作为催化剂。此外，还建立了一个独特的还原体系，以解决必要的 PIII/PV = O 氧化还原循环。通过计算和实验相结合的研究，阐明了手性双膦催化不对称 Staudinger/aza-Wittig 反应的机理。利用新开发的方法，简明地合成了几种克林类金丝桃科生物碱。

引用次数: 0

Enantioselective Oxidative Homocoupling of 2-Oxindoles with a Chiral Bisguanidinium Hypoiodite Catalyst 用手性次碘酸双胍催化剂对 2-氧化吲哚进行对映选择性氧化偶联反应

IF 2 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-08-20 DOI: 10.1055/s-0043-1775056

Minami Odagi, Yuta Shimizu, Kota Sugimoto, Io Mori, Ban Xu, Choon Hong Tan, Kazuo Nagasawa

The bisoxindole motif is present in a variety of biologically active compounds. Here, we report an enantioselective oxidative homocoupling reaction of 2-oxindoles in the presence of a chiral bisguanidinium hypoiodite catalyst, providing access to the corresponding optically active bisoxindoles in excellent yields and with moderate to high diastereo- and enantioselectivities.

双吲哚基团存在于多种具有生物活性的化合物中。在此，我们报告了在手性双胍基次碘酸催化剂存在下，2-氧化吲哚的对映体选择性氧化同偶联反应，以优异的产率和中等至高的非对映及对映体选择性获得了相应的光学活性双氧化吲哚。

引用次数: 0

Thiuram Disulfide Mediated Copper-Catalyzed C–S Cross-Coupling: Synthesis of S-Thiocarbamate Compounds 二硫化秋兰姆介导的铜催化 C-S 交叉偶联：S-Thiocarbamate 化合物的合成

IF 2 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-08-19 DOI: 10.1055/a-2375-7696

Sourav Mondal, Debabrata Patra, Amit Saha

Thiuram disulfides undergo a Cu(I)-catalyzed C–S cross-coupling with aryl iodides through Cu(OAc)₂·H₂O-assisted desulfurization to produce the S-thiocarbamate ester compounds efficiently. Various aryl iodides containing diverse substituents underwent a smooth reaction with a series of cyclic and acyclic secondary amine-based thiuram disulfides under an open-air atmosphere. A probable mechanistic pathway has been suggested based on control experiments and reports from the literature.

通过 Cu(OAc)2-H2O 辅助脱硫，秋兰姆二硫化物在 Cu(I)催化下与芳基碘化物发生 C-S 交叉偶联反应，从而高效生成 S-硫代氨基甲酸酯化合物。在露天气氛下，含有不同取代基的各种芳基碘化物与一系列环状和非环状仲胺基秋兰二硫化物发生了顺利反应。根据对照实验和文献报道，提出了一种可能的机理途径。

引用次数: 0

1,2-Diaroyl Benzofurans: Synthesis and Photochromic Properties 1,2-二芳基苯并呋喃：合成与光致变色特性

IF 2 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-08-15 DOI: 10.1055/s-0043-1775039

Jianming Zhong, Shuangshuang Li, Zhaoxin Wang, Wang Zhou

A cascade reaction involving a base-promoted nucleophilic substitution reaction between diketones and α-bromoacetophenone derivatives and the subsequent selective condensation–cyclization was developed for the synthesis of 1,2-diaroyl benzofurans. 1,2-Diaroyl benzofurans with different functional groups and structures exhibit reversible photochromic behaviors in solution, solid state, and thin films with diverse colors, demonstrating a potential application in the field of optical functional materials.

为了合成 1,2-二芳基苯并呋喃，研究人员开发了一种级联反应，包括二酮和α-溴苯乙酮衍生物之间的碱促进亲核取代反应以及随后的选择性缩合-环化反应。具有不同官能团和结构的 1,2-二芳基苯并呋喃在溶液、固态和薄膜中表现出可逆的光致变色行为，并呈现出不同的颜色，显示了其在光学功能材料领域的应用潜力。

引用次数: 0

Ketocalixarenes: Versatile yet still Unexplored Macrocycles 酮钙烯烃：用途广泛但仍未开发的大环

IF 2 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-08-12 DOI: 10.1055/s-0043-1775380

Ori Shalev, Silvio E. Biali

Ketocalix[n]arenes can be prepared via oxidation of the methylene groups of protected calix[n]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[n]radialenes.

1 Introduction

2 Synthesis of Ketocalix[n]arenes

2.1 Ketocalix[4]arene Derivatives

2.2 Systems Possessing both Carbonyl and Bromomethane Bridges

2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives

2.4 Monooxo- and Dioxoketocalix[6]arenes

3 Conformation of Ketocalixarenes

4 Reactions of Ketocalixarenes

4.1 Alkylation of the OH Groups

4.2 Intramolecular Aromatic Nucleophilic Substitution

4.3 Reduction of the Carbonyl Groups

4.4 Reaction of 5c with PhLi

4.5 Reaction with tert-Butyllithium

5 From Ketocalix[n]arenes to Calix[n]radialenes and Calix[n]rotanes

6 Summary and Outlook

通过氧化受保护的钙并[n]烯的亚甲基，可以制备酮钙并[n]烯。桥上羰基的存在改变了大环的优选构象和反应活性，并（通过亲核加成反应）为多种亚甲基取代衍生物以及钙并[n]辐射烯提供了切入点。1 引言 2 Ketocalix[n]arenes 的合成 2.1 Ketocalix[4]arene 衍生物 2.2 同时具有羰基和溴甲烷桥的体系 2.3 Pentaoxoketocalix[5]arene 和 Hexaoxoketocalix[6]arene 衍生物 2.4 Monooxo- 和 Dioxoketocalix[6]arenes 3 Ketocalixarenes 的构象 4 Ketocalixarenes 的反应 4.1 OH 基团的烷基化 4.2 分子内芳香族亲核取代 4.3 羰基的还原 4.4 5c 与 PhLi 的反应 4.5 与叔丁基锂的反应 5 从 Ketocalix[n]arenes 到 Calix[n]radialenes 和 Calix[n]rotanes 6 小结与展望

引用次数: 0

Reductive Electrophilic Cross-Coupling for Constructing C(sp3)–C(sp3) Bonds 构建 C(sp3)-C(sp3)键的还原亲电交叉偶联反应

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-07-25 DOI: 10.1055/a-2373-0471

Pengfei Li, Youai Qiu

C(sp3)-C(sp3) bond is one of the most prevalent motifs in organic compounds and holds significant importance in organic synthesis. The utilization of two alkyl electrophiles for cross-coupling stands as a vital strategy in building C(sp3)–C(sp3) bonds. Nowadays, synthetic electrochemistry is undergoing rapid development owing to its exceptional attributes not only in terms of green and economic properties by reducing the large amount of traditional chemical reductants, but also by its capacity to generate highly reactive radical intermediates under mild conditions, thereby opening up new reaction pathways and presenting novel opportunities to constructing C(sp3)-C(sp3) bonds. This article aims to comprehensively delineate the historical development of traditional electrophilic reagents in constructing C(sp3)-C(sp3) bonds, while also delving into the advantages of electrochemical electrophilic cross-coupling in this domain.

C(sp3)-C(sp3)键是有机化合物中最常见的主题之一，在有机合成中具有重要意义。利用两个烷基亲电体进行交叉耦合是建立 C(sp3)-C(sp3)键的重要策略。如今，合成电化学正处于快速发展阶段，因为它不仅具有减少大量传统化学还原剂的绿色经济特性，还能在温和条件下生成高活性自由基中间体，从而开辟新的反应途径，为构建 C(sp3)-C(sp3)键提供新的机会。本文旨在全面阐述传统亲电试剂在构建 C(sp3)-C(sp3)键方面的历史发展，同时深入探讨电化学亲电交叉偶联在这一领域的优势。

引用次数: 0

Synthesis of Bifluorenylidene- and Cycloocta[1,2,3-jk:6,5,4-j'k']difluorene-Extended Tetrathiafulvalenes – Novel Multi-Redox Systems 双芴和环辛并[1,2,3-jk:6,5,4-j'k']二芴--新型多重氧化还原体系的合成

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-07-25 DOI: 10.1055/a-2373-0422

Jonathan Kirschner Solberg Hansen, Mogens Brøndsted Nielsen

Herein, we present the synthesis of a novel 9,9’-bifluorenylidene-extended tetrathiafulvalene (TTF) as an E/Z isomeric mixture that was found to readily undergo an oxidative dimerization to furnish a TTF vinylogue with the two dithiafulvene units connected to an eight-membered ring fused to a bifluorenylidene core. This compound exhibited multi-redox behavior and was found to take six charge states under cyclic voltammetry conditions: -2, -1, 0, +1, +2, +3. The dication corresponds to a cycloocta[1,2,3-jk:6,5,4-j’k’]difluorene with two appended 1,3-dithiolium rings.

在本文中，我们合成了一种新型 9,9'-联芴基扩展四硫富戊烯（TTF）的 E/Z 异构体混合物，发现该混合物很容易发生氧化二聚反应，生成一种 TTF 乙烯基对映体，其中两个二硫富戊烯单元连接到一个与联芴基核心融合的八元环上。这种化合物具有多重氧化还原行为，在循环伏安法条件下可产生六种电荷状态：-这种二阳离子对应于带有两个附加 1,3 二硫环的环辛基[1,2,3-jk:6,5,4-j'k']二芴。

引用次数: 0

Studies toward the synthesis of Colletotrichamide A: Construction of C19-C30 Segment of the Molecule 关于合成可乐丽酰胺 A 的研究：构建分子的 C19-C30 段

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-07-25 DOI: 10.1055/a-2373-0372

Nemilikonda Sravan Kumar, Radhakrishna Gattu, B. J. Ramulu, Subhash Ghosh

The synthesis of C19–C30 segment of the neuroprotective natural product colletotrichamide A has been achieved by performing Sonogashira coupling between the fragments 9 and 10. Maruoka-Keck allylation, Evans syn-aldol and Takai olefinations were used as the key steps for fragment 9 whereas glycosidation and Ohira-Bestmann reactions were used as the pivotal steps for accessing fragment 10.

通过在片段 9 和 10 之间进行 Sonogashira 偶联，合成了具有神经保护作用的天然产物可乐三色酰胺 A 的 C19-C30 片段。片段 9 的关键步骤是 Maruoka-Keck烯丙基化反应、Evans syn-aldol 反应和 Takai 烯化反应，而片段 10 的关键步骤是糖苷化反应和 Ohira-Bestmann 反应。

引用次数: 0

Chemo- and regioselective demethylation of 2-bromo-α-resorcylic acid derivatives using alkylthiolate salts 使用烷基硫代酸盐对 2-溴-α-去甲酰基酸衍生物进行化学和区域选择性去甲基化反应

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-07-22 DOI: 10.1055/a-2370-7112

Tommy Fraser, Zakiel Harbour, N. Voyer, Sébastien Cardinal

We report here the chemo- and regioselective demethylation of 3,5-dimethoxy-2-bromo-α-resorcylic acid esters by a thiolate nucleophilic displacement reaction. Optimized conditions facilitate yields up to 93% for o-bromo selective demethylation of diverse ester derivatives of dimethoxy 2-bromo-α-resorcylic acid. Our results highlight a new, efficient, and reliable demethylation reagent, as well as a useful steric bias directing strategy.

我们在此报告通过巯基亲核置换反应对 3,5-二甲氧基-2-溴-α-resorcylic 酸酯进行化学和区域选择性去甲基化的情况。经过优化的条件可使邻溴选择性脱甲基化 2-溴-α-resorcylic acid 的各种酯衍生物的收率高达 93%。我们的研究结果凸显了一种新型、高效、可靠的去甲基化试剂，以及一种有用的立体偏置引导策略。

引用次数: 0

Transition metal-free approach for the synthesis of N-arylated piperidones and its ketals from ketenedithioacetal 从二硫代乙醛合成 N-芳基哌啶酮及其酮类的无过渡金属方法

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett

Pub Date : 2024-07-22 DOI: 10.1055/a-2370-6625

Ramendra Pratap, S. Sahu, Ranjay Shaw, Ismail Althagafi

N-Arylated piperidones were present as pharmacophores in many pharmaceuticals and useful precursors for the construction of new important molecules. We have developed a transition metal-free, cost-effective and mild approach for the synthesis of N-arylated/heteroarylated piperidones and its ketal by using ketal of piperidones and 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles as precursors. The desired product was achieved in 2 steps including amination of 2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles from piperidone followed by ring transformation using a suitable nucleophile source. We have successfully tethered functionalized dihydrophenanthrenes, hydrobenzo[c]phenanthrenes and benzoquinolines at N-piperidinone under transition metal free conditions.

N-芳基化哌啶酮是许多药物的药源，也是构建新的重要分子的有用前体。我们以哌啶酮酮化物和 2-氧代-5,6-二氢-2H-苯并[h]色烯-3-甲腈为前体，开发了一种无过渡金属、低成本、温和的方法来合成 N-芳基化/异芳基化哌啶酮及其酮化物。我们分两步获得了所需产物，包括先将 2-氧代-5,6-二氢-2H-苯并[h]色烯-3-甲腈与哌啶酮胺化，然后使用合适的亲核剂进行环转化。在无过渡金属条件下，我们成功地在 N-哌啶酮上拴系了官能化的二氢菲、氢苯并[c]菲和苯并喹啉。

引用次数: 0

首页上一页

下一页尾页

类型

全部化学•材料生命科学医学物理工程技术环境•农林材料科学地球科学法学管理学化学环境科学与生态学计算机科学教育学经济学农林科学人文科学生物学数学物理与天体物理心理学综合性期刊其他工业工程理学历史学农学文学信息工程

数据库

全部 ACS Publications Elsevier ieeexplore Springer The Royal Society of Chemistry Wiley

期刊

Synlett

全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.

﹀