Photoredox‐Catalyzed α−C−H Monoalkylation of Symmetric Polyols in the Presence of CO2 DOI

Gaétan Archer,

Ricardo Meyrelles,

Isabel Eder

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(6)

Опубликована: Дек. 13, 2023

Abstract Achieving the selective modification of symmetric poly‐hydroxylated compounds presents a significant challenge due to presence identical active sites. Herein, we address this through design ternary catalytic system that includes photoredox catalyst, hydrogen atom transfer promotor and carbonation catalyst. This enables reversible acyclic polyols under CO 2 atmosphere, which modulates reactivity its distinct C−H bonds toward transfers. An exquisite selectivity for monoalkylation is achieved in variety unprotected light polyols, yielding valuable building blocks short reaction times. Mechanistic computational studies demonstrate formation an intramolecular bond between transient carbonate free alcohol pivotal kinetic thermodynamic activation specific alcohol.

Язык: Английский

Photoredox‐Catalyzed α−C−H Monoalkylation of Symmetric Polyols in the Presence of CO2 DOI

Gaétan Archer,

Ricardo Meyrelles,

Isabel Eder

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(6)

Опубликована: Дек. 13, 2023

Abstract Achieving the selective modification of symmetric poly‐hydroxylated compounds presents a significant challenge due to presence identical active sites. Herein, we address this through design ternary catalytic system that includes photoredox catalyst, hydrogen atom transfer promotor and carbonation catalyst. This enables reversible acyclic polyols under CO 2 atmosphere, which modulates reactivity its distinct C−H bonds toward transfers. An exquisite selectivity for monoalkylation is achieved in variety unprotected light polyols, yielding valuable building blocks short reaction times. Mechanistic computational studies demonstrate formation an intramolecular bond between transient carbonate free alcohol pivotal kinetic thermodynamic activation specific alcohol.

Язык: Английский

Процитировано

4
Recent Progress in the Synthesis and Glycosylation of Rare Sugars DOI Creative Commons
Nicole Hauser, Marvin Wenninger,

Martin L. Poulsen

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 8, 2024

Abstract Out of 42 naturally occurring monosaccharides, only seven are abundant in Nature (glucose, galactose, mannose, fructose, xylose, ribose, and l-arabinose), while the others have been classified as ‘rare sugars’. Fungi bacteria use a wide range contrast to mammals, reflected their glycosylated metabolites, well cellular machineries that involved sugar metabolism. Recognition microbiome’s impact on human health has led increased interest microbial glycans, they often mediate interaction between host microbes. Efficient access rare sugars oligosaccharides is necessary study roles Nature, which can provide new pharmacological leads. Furthermore, it enables synthesis bioactive natural products congeners. This short review highlights recent progress efficient, site- stereoselective glycosylation sugars. Finally, provides example where synthetic enabled biochemical studies better understand interfere with processes Nature. 1 Introduction 2 Synthesis Rare Sugars 2.1 Syntheses from Renewable Feedstock 2.2 De Novo 3 Glycosylation 3.1 Catalyst-Controlled 3.2 One-Pot Iterative Oligosaccharide Solution 4 Application Biochemical Research 5 Conclusion

Язык: Английский

Процитировано

1
Site‐Selective Electrochemical Oxidation of Carbohydrates DOI Creative Commons

Elisa Kapetanović,

Sebastian B. Beil

ChemElectroChem, Год журнала: 2023, Номер 10(22)

Опубликована: Окт. 19, 2023

Abstract The site‐selective transformation of unprotected sugars poses significant challenges to synthetic chemists but comes with a reward step‐economic and energy efficient protocols. By replacing stoichiometric oxidants electricity, greener processes are anticipated. To date, mostly C3‐ C6‐selective transformations have been developed urging for further developments. Herein, we call action tackle the associated toward challenging C2 C4 regioisomers fueled by mild electroorganic transformations.

Язык: Английский

Процитировано

1
Zucker elektrochemisch oxidieren DOI
Sebastian B. Beil

Nachrichten aus der Chemie, Год журнала: 2024, Номер 72(1), С. 67 - 69

Опубликована: Янв. 1, 2024

Abstract Früher war organische Elektrochemie selten selektiv und mit technischen Hürden verbunden, heute ist sie oft die einfachste Option, um Zucker zu oxidieren. Dabei wählerisch – denn eine der drei sekundären Hydroxygruppen von Glucosiden anders als anderen.

Процитировано

0
Site-selective editing of carbohydrate scaffolds to access rare sugars enabled by photoinduced radical processes DOI
Liwen Xia, Qingqin Huang, Lei Dai

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4926 - 4933

Опубликована: Янв. 1, 2024

Herein, we summarize recent achievements via photoinduced radical-mediated strategies that enable the precise modification of carbohydrates.

Язык: Английский

Процитировано

0
Photoredox‐Catalyzed α−C−H Monoalkylation of Symmetric Polyols in the Presence of CO2 DOI

Gaétan Archer,

Ricardo Meyrelles,

Isabel Eder

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 136(6)

Опубликована: Дек. 13, 2023

Abstract Achieving the selective modification of symmetric poly‐hydroxylated compounds presents a significant challenge due to presence identical active sites. Herein, we address this through design ternary catalytic system that includes photoredox catalyst, hydrogen atom transfer promotor and carbonation catalyst. This enables reversible acyclic polyols under CO 2 atmosphere, which modulates reactivity its distinct C−H bonds toward transfers. An exquisite selectivity for monoalkylation is achieved in variety unprotected light polyols, yielding valuable building blocks short reaction times. Mechanistic computational studies demonstrate formation an intramolecular bond between transient carbonate free alcohol pivotal kinetic thermodynamic activation specific alcohol.

Язык: Английский

Процитировано

0