☆ 4.8 Article

Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2-Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷 47, 期 46, 页码 8917-8919

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.200803696

关键词

1,2-diketones; aldol reaction; carbohydrates; photochemistry; radicals

类别

Chemistry, Multidisciplinary

资金

Ministerio de Educacion y Ciencia, Spain [CTQ2004-06381/BQU, CTQ2004-02367/BQU, CTQ2007-67492/BQU]
Fondo Europeo de Desarrollo Regional (FEDER)

向作者/读者索取更多资源

Protocol

Reagent

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Multidisciplinary

Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center

Zexian Li, Minyan Wang, Zhuangzhi Shi

Summary: An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed, generating valuable multisubstituted perfluoroalkylated compounds in a single step. Mechanistically, photoinduced alkyl radical addition to an alkene leads to migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center, followed by generation of a C-radical bearing two electron-withdrawing groups and reduction by a hydrogen donor to complete the domino sequence.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis

Yuan-Yuan Cheng, Ji-Xin Yu, Tao Lei, Hong-Yu Hou, Bin Chen, Chen-Ho Tung, Li-Zhu Wu

Summary: This study presents the first example of 1,2-dicarbonylation of alkenes by photocatalysis, achieving unsymmetric 1,4-dicarbonylation by tuning the reductive and electrophilic ability of the acyl precursor. The metal-free, redox-neutral and regioselective reaction shows great potential in biomolecular and drug molecular derivatization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light Photoredox-Catalyzed Divergent 1,2-Diacylation and Hydroacylation of Alkenes with Carboxylic Acid Anhydride

Youkang Zhou, Lirong Zhao, Mingyou Hu, Xin-Hua Duan, Le Liu

Summary: In this study, a photoredox-catalyzed divergent 1,2-dicarbonylation and hydroacylation of alkenes with acid anhydride was presented. This approach provides a mild and efficient method for synthesizing 1,4-dicarbonyl compounds bearing all-carbon quaternary centers, demonstrating a broad substrate scope and high functional group compatibility. Hydrocarbonylation of alkenes can also be achieved by introducing a proton source to the reaction system. Mechanistic investigations support a radical addition/radical-polar crossover cascade.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Remote C-H Pyridylation of Hydroxamates through Direct Photoexcitation of O-Aryl Oxime Pyridinium Intermediates

Byeongseok Kweon, Changha Kim, Seonyul Kim, Sungwoo Hong

Summary: An efficient strategy for remote C-H pyridylation of hydroxamates with excellent ortho-selectivity has been developed by designing new photon-absorbing O-aryl oxime pyridinium salts. The photoexcitation of oxime pyridinium intermediates generates iminyl radicals via photolytic N-O bond cleavage, allowing for the installation of pyridyl rings at the gamma-CN position. This novel synthetic approach offers advantages in terms of efficiency, simplicity, and broad functional group tolerance under mild and metal-free conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines

Dilip Patil, Tengda Si, Hun Young Kim, Kyungsoo Oh

Summary: The study for the first time disclosed the generation of aminium radical cation species from N-nitrosoamines through visible-light excitation at 453 nm, and achieved the photoaddition reaction of N-nitrosoamines to alkenes. By combining the aerobic oxidation protocol of amines, the one-pot synthesis of aamino oxime derivatives was successfully realized in a tandem N-nitrosation and photoaddition sequence.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Photoalkylation/-arylation of ortho-Diketones with Unactivated Organic Halides

Xiao-Yu Wang, Yong-Qin He, Yi Zhou, Lin Lu, Xian-Rong Song, Zhao-Zhao Zhou, Wan-Fa Tian, Qiang Xiao

Summary: This article presents a new method for reductive alkylation/arylation of 1,2-diketones using visible light and unactivated organic halides. The technique does not require a photocatalyst and utilizes Et3N as a promoter. Et3N generates a ketyl radical and an alpha-aminoalkyl radical, which activate C-X bonds through a halogen atom transfer process (XAT). The use of Et3N as a promoter allows for expanding the range of organic halide substrates, including primary, secondary, and aromatic organic halides, and various functional groups.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Organic

Visible Light Induced Solubility Modulation of Polynorbornene Bearing Bridged 1,2-Diketones

Kyungrae Kim, Donghwa Seo, Dowan Kim, Jeewoo Lim

Summary: The study reports the synthesis of a polymer with bridged 1,2-diketone units and the photoinduced solubility modulation method. By irradiating the monomer with a blue LED light source at a specific wavelength, rapid change in molecular structure and solubility modulation were achieved.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Physical

Protonated Chiral 1,2-Diamine Organocatalysts for N-Selective Nitroso Aldol Reaction

Jae Ho Shim, Ji Yeon Lee, Hyeon Soo Kim, Deok-Chan Ha

Summary: The study developed a catalyst with N-selectivity for the nitroso aldol reaction, using a quantum calculation. The reaction mechanism was determined and optimized, resulting in a high yield of the product with high enantioselectivity. The catalyst provides a less expensive and more environmentally friendly alternative for the reaction.

CATALYSTS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Dynamic Kinetic Resolution of β-Substituted α-Diketones via Asymmetric Transfer Hydrogenation

Ting Chen, Wenjun Liu, Wei Gu, Shengtong Niu, Shouang Lan, Zhifei Zhao, Fan Gong, Jinggong Liu, Shuang Yang, Andrej Emanuel Cotman, Jinshuai Song, Xinqiang Fang

Summary: In this study, a unique dynamic kinetic resolution (DKR) mode was used to achieve the highly selective semi-transfer hydrogenation of unsymmetrical alpha-diketones. The distal carbonyl group was reduced while the proximal carbonyl remained untouched, resulting in the synthesis of enantioenriched acyclic ketones with alpha-hydroxy-alpha'-C(sp2)-functional groups. These products represent a new class of compounds that have not been previously reported. The utility of the synthesized compounds was demonstrated through further transformations, including the rapid synthesis of drug molecules. DFT calculations and control experiments were conducted to gain mechanistic insights into the highly selective semihydrogenation.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Imidazoles from Fatty 1,2-Diketones

Mansouria Bouchakour, Mortada Daaou, Nicolas Duguet

Summary: Unsaturated vegetable oils were used to prepare fatty imidazoles through the Debus-Radziszewski reaction, which was optimized under microwave irradiation. The reaction yielded the desired imidazoles at a high GC yield of 96% when using benzaldehyde as a model substrate at 180 degrees C for 5 minutes. Various aldehydes were tested under the optimized conditions, resulting in isolated yields of 33-99% for the corresponding imidazoles.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Organic

Transition Metal-Catalyzed Synthesis of 1,2-Diketones: An Overview

Atul Kumar, Vellaisamy Sridharan

Summary: The 1,2-diketone structural motif is commonly found in natural products and biologically significant compounds, serving as precursors or intermediates in important organic transformations. Transition-metal catalysis is essential for generating carbon-carbon and carbon-heteroatom bonds to access diverse heterocyclic compounds, and has been frequently used for the synthesis of valuable 1,2-diketones from easily accessible starting materials.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic chemodivergent annulations between α-diketones and alkynyl α-diketones

Xiangwen Kong, Fang Yu, Zhizhou Chen, Fan Gong, Shuang Yang, Jinggong Liu, Benlong Luo, Xinqiang Fang

Summary: This study has successfully achieved four unprecedented and chemodivergent reactions between alpha-diketones and alkynyl alpha-diketones, leading to the construction of various biologically important molecular scaffolds. The products also exhibit promising photophysical properties and application potential, demonstrating the great value of alpha-diketones in both synthetic chemistry and material science.

SCIENCE CHINA-CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic Asymmetric Cascade Michael-acyl Transfer Reaction between 2-Fluoro-1,3-diketones and Unsaturated Thiazolones: Access to Fluorinated 4-Acyloxy Thiazoles

Rayhan G. Biswas, Sumit K. Ray, Rajshekhar A. Unhale, Vinod K. Singh

Summary: A bifunctional urea catalyzed cascade reaction of 5-alkenyl thiazolones and monofluorinated beta-diketones, derived from quinine, has been developed, yielding fluorine containing 4-acyloxy thiazoles with high yields and good diastereo- and excellent enantioselectivities. Synthetic transformations, including the synthesis of 4-hydroxy thiazoles, have been successfully demonstrated.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

Photocatalytic Alkylation/Arylative Cyclization of N-Acrylamides of N-Heteroarenes and Arylamines with Dihydroquinazolinones from Unactivated Ketones

Sandip Bag, Shubham Ojha, Sreelakshmi Venugopalan, Basudev Sahoo

Summary: In this study, we present a visible-light photoredox-catalyzed alkylation/arylative cyclization reaction of N-acrylamides with ketone-derived dihydroquinazolinones. This method allows the formation of indolo- and benzimidazolo[2,1-a]isoquinolines or 2-oxindoles from 2-arylindoles, 2-arylbenzimidazoles, or N-substituted anilines. The reaction proceeds through the formal cleavage of ketone α-C-C and arene C-H bonds, leading to the incorporation of alkyl and aryl carbogenic motifs and the synthesis of cyclic structures with a quaternary stereocenter.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Regio- and Stereoselectivity of the Norrish-Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

Dimitri Alvarez-Dorta, Elisa Leon, Angeles Martin, Alan R. Kennedy, Ines Perez-Martin, Kenneth Shankland, Ernesto Suarez

Summary: The research shows that the regioselectivity of the Norrish-Yang type II photocyclization dramatically increases in the crystalline state of both polymorphs of 3 beta-acetoxy-16,17-seco-17,20-dioxopregn-5-ene-16-nitrile. X-ray crystallography and molecular mechanics calculations reveal crystal structure-solid state photochemistry relationships.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Reductive Radical Cascades Triggered by Alkoxyl Radicals in the beta-Cyclodextrin Framework

Elisa I. Leon, Angeles Martin, Ines Perez-Martin, Ernesto Suarez

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling

Dimitri Alvarez-Dorta, Christine Thobie-Gautier, Mikael Croyal, Mohammed Bouzelha, Mathieu Mevel, David Deniaud, Mohammed Boujtita, Sebastien G. Gouin

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Organic

Synthetic Approaches to Phosphasugars (2-oxo-1,2-oxaphosphacyclanes) Using the Anomeric Alkoxyl Radical beta-Fragmentation Reaction as the Key Step

Daniel Hernandez-Guerra, Alan R. Kennedy, Elisa Leon, Angeles Martin, Ines Perez-Martin, Maria S. Rodriguez, Ernesto Suarez

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Tyrosine Conjugation Methods for Protein Labelling

Dimitri Alvarez Dorta, David Deniaud, Mathieu Mevel, Sebastien G. Gouin

CHEMISTRY-A EUROPEAN JOURNAL (2020)

添加到收藏夹

Article Electrochemistry

Simulation of the environmental degradation of diuron (herbicide) using electrochemistry coupled to high resolution mass spectrometry

Ranil C. T. Temgoua, Ugo Bussy, Dimitri Alvarez-Dorta, Nicolas Galland, Julie Hemez, Ignas K. Tonle, Mohammed Boujtita

ELECTROCHIMICA ACTA (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Polyvalent Transition-State Analogues of Sialyl Substrates Strongly Inhibit Bacterial Sialidases

Coralie Assailly, Clarisse Bridot, Amelie Saumonneau, Paul Lottin, Benoit Roubinet, Eva-Maria Krammer, Francesca Francois, Federica Vena, Ludovic Landemarre, Dimitri Alvarez Dorta, David Deniaud, Cyrille Grandjean, Charles Tellier, Sagrario Pascual, Veronique Montembault, Laurent Fontaine, Franck Daligault, Julie Bouckaert, Sebastien G. Gouin

Summary: In this study, researchers developed multi- and polyvalent compounds capable of inhibiting bacterial sialidases. These compounds show a higher inhibitory potential than monovalent analogues, and exhibit a synergistic interaction in the catalytic domain. These results offer interesting perspectives for multivalent inhibition of other SA families lacking a carbohydrate-binding module.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

添加到收藏夹

Article Chemistry, Analytical

Using electrochemistry coupled to high resolution mass spectrometry for the simulation of the environmental degradation of the recalcitrant fungicide carbendazim

Ranil C. T. Temgoua, Ugo Bussy, Dimitri Alvarez-Dorta, Nicolas Galland, Julie Hemez, Christine Thobie-Gautier, Ignas Kenfack Tonle, Mohammed Boujtita

Summary: The study focuses on the electrochemical behavior/degradation of the carbendazim (CBZ) fungicide, with the use of EC-LC-MS and EC-MS analysis to identify new degradation products such as a quinone imine and a nitrenium ion. This hyphenated technique proved to be a rapid and reliable tool to elucidate the oxidative degradation of CBZ.

TALANTA (2021)

添加到收藏夹

Article Chemistry, Organic

1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems

Elisa Leon, Angeles Martin, Adrian S. Montes, Ines Perez-Martin, Maria del Sol Rodriguez, Ernesto Suarez

Summary: The study investigates a radical/polar sequence triggered by alkoxyl radicals in 1,5-HAT-1,2-(ester)alkyl radical migration, leading to the efficient construction of complex carbohydrate frameworks. Attention was given to the influence of stereochemistry on the reaction outcome. The addition of BF3·Et2O catalyst significantly increased the yields of desired bicyclic ketals.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Free-Radical Epimerization of d- into l-C-(Glycosyl)methanol Compounds Using 1,5-Hydrogen Atom Transfer Reaction

Adrian S. Montes, Elisa Leon, Angeles Martin, Ines Perez-Martin, Ernesto Suarez

Summary: A simple method for the epimerization of C-(alpha-d-Glyp)methanol into C-(beta-l-Glyp)methanol compounds is described in this study. The reaction involves radical cleavage of the C5-H bond by 1,5-hydrogen atom transfer followed by hydride addition with inversion of configuration. This methodology allows the synthesis of rare C-(beta-l-Idop)-, C-(beta-l-Altp)-, C-(beta-l-Gulp)-, C-(beta-l-Allp)methanol glycosides starting from d-series carbohydrates. It can also be used to transform l-configured C-glycosyl compounds to d-configured ones. The synthesis of C-(beta-d-6dGulp)- and C-(beta-d-6dAltp)methanol from readily accessible l-rhamno and l-fuco analogs, respectively, demonstrates the applicability of this method. Furthermore, compounds with C-(beta-l-Araf)- and C-(beta-l-5dRibf)methanol structures have also been synthesized. The influence of sugar ring conformation and substituent electronegativity on the stereochemical outcome is discussed based on experimental results.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Regio- and Stereoselectivity of the Norrish-Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

Dimitri Alvarez-Dorta, Elisa Leon, Angeles Martin, Alan R. Kennedy, Ines Perez-Martin, Kenneth Shankland, Ernesto Suarez

Summary: The research shows that the regioselectivity of the Norrish-Yang type II photocyclization dramatically increases in the crystalline state of both polymorphs of 3 beta-acetoxy-16,17-seco-17,20-dioxopregn-5-ene-16-nitrile. X-ray crystallography and molecular mechanics calculations reveal crystal structure-solid state photochemistry relationships.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins

Sebastien Depienne, Dimitri Alvarez-Dorta, Mikael Croyal, Ranil C. T. Temgoua, Cathy Charlier, David Deniaud, Mathieu Mevel, Mohammed Boujtita, Sebastien G. Gouin

Summary: This study evaluated the limitations, benefits, and relative efficiencies of eY-click conjugations using PhUr, NMePhUr, and NMeLum derivatives. NMeLum demonstrated high efficiency and complete Y-chemoselectivity on polypeptides and biologically relevant proteins after soft electrochemical activation. Side reactions on nucleophilic or heteroaromatic amino acids were never observed during mass spectrometry analysis.

CHEMICAL SCIENCE (2021)

添加到收藏夹

Article Chemistry, Analytical

Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides

Ranil Clement Tonleu Temgoua, Ugo Bussy, Dimitri Alvarez-Dorta, Nicolas Galland, Evangeline Njanja, Julie Hemez, Christine Thobie-Gautier, Ignas Kenfack Tonle, Mohammed Boujtita

Summary: In this study, an alternative non-enzymatic method using electrochemistry coupled to liquid chromatography-high resolution mass spectrometry-DFT theoretical calculations was proposed for simulating the environmental degradation of phenylurea herbicides and elucidating their mechanism. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. This method successfully mimicked various reactions and provided useful insights for understanding and predicting the oxidative degradation pathways of pesticides in the environment.

ENVIRONMENTAL SCIENCE-PROCESSES & IMPACTS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chemical modification of the adeno-associated virus capsid to improve gene delivery

Mathieu Mevel, Mohammed Bouzelha, Aurelien Leray, Simon Pacouret, Mickael Guilbaud, Magalie Penaud-Budloo, Dimitri Alvarez-Dorta, Laurence Dubreil, Sebastien G. Gouin, Jean Philippe Combal, Mirja Hommel, Gloria Gonzalez-Aseguinolaza, Veronique Blouin, Philippe Moullier, Oumeya Adjali, David Deniaud, Eduard Ayuso

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Multivalency To Inhibit and Discriminate Hexosaminidases

Dimitri Alvarez-Dorta, Dustin T. King, Thibaut Legigan, Daisuke Ide, Isao Adachi, David Deniaud, Jerome Desire, Atsushi Kato, David Vocadlo, Sebastien G. Gouin, Yves Bleriot

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.