Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles

Risi, Caterina; Zhao, Fei; Castagnolo, Daniele

doi:10.1021/acscatal.9b02452

Cited by 41 publications

(21 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequent Ru‐catalysed metathesis yielded the corresponding stilbene compounds of interest. Finally, Castagnolo and coworkers have recently combined 2 nd generation Grubbs catalyst‐mediated ring‐closing metathesis of diallyl ethers and laccase/TEMPO catalysed aromatisation to produce furans (Scheme 3b) [47] . The cascade was run in a one‐pot two‐step manner, with isooctane as the cosolvent in a two‐phase system to prevent enzyme deactivation caused by the metal catalyst.…”

Section: Linear Cascades Combining Transition Metal Catalysis and Bio...mentioning

confidence: 99%

Construction of Chemoenzymatic Linear Cascades for the Synthesis of Chiral Compounds

Ascaso-Alegre

MANGAS

2022

Eur J Org Chem

View full text Add to dashboard Cite

Juan Mangas Sanchez was nominated to be part of this collection by EurJOC Board Member Silvia Osuna OliverasInspired by nature, synthetic chemists try to mimic the efficient metabolic networks in living organisms to build complex molecules by combining different types of catalysts in the same reaction vessel. These multistep cascade processes provide many advantages to synthetic procedures, resulting in higher productivities with lower waste generation and cost. However, combining different chemo-and biocatalysts can be challenging as reaction conditions might differ greatly. As a highly multidisciplinary field that benefits from advances in chemical catalysis, molecular biology and reaction engineering, this area of study is rapidly progressing. In this Review, we highlight recent trends and advances in the construction of multistep chemoenzymatic one-pot cascades to access chiral compounds as well as the different strategies to solve current challenges in the field.

show abstract

Section: Linear Cascades Combining Transition Metal Catalysis and Bio...mentioning

confidence: 99%

Construction of Chemoenzymatic Linear Cascades for the Synthesis of Chiral Compounds

Ascaso-Alegre

MANGAS

2022

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…131 In 2019, Castagnolo et al reported the aerobic chemoenzymatic aromatization of 2,5-dihydrofurans, which was synthesized by ring-closing metathesis of diallyl ether, using laccase-TEMPO catalytic system. 132 In 2020, Hamada et al reported the catalytic chemoselective cleavage of p-methoxybenzyl ethers using their electronically tuned nitroxyl radical. 133 They expanded the utility of the electronically tuned nitroxyl radical to the catalytic oxidation of cyclic ethers.…”

Section: -3-1 C-h Oxidation and C-o Cleavage Of Ethers (Scheme 17)mentioning

confidence: 99%

The Utility of Oxoammonium Species in Organic Synthesis: Beyond Alcohol Oxidation

Iwabuchi¹,

Nagasawa²

2022

HETEROCYCLES

View full text Add to dashboard Cite

Oxoammonium species are electrophilic chemical species generated via single electron oxidation of nitroxyl radicals. Although this species and its salts are known as useful oxidants and active species for (catalytic) oxidation of alcohols into carbonyl compounds in organic synthesis, the benefits of oxoammonium species for the oxidative transformations of numerous types of substrates apart from alcohols has been reported. This review summarizes the synthetic utility of oxoammonium species under both stoichiometric and catalytic conditions with the exception of alcohol oxidation. CONTENTS 1. Introduction 2. Oxoammonium species 3. Oxoammonium species (salt)-mediated oxidative transformation 3-1. Oxidative esterification/amidation 3-2. Oxidation of amines (imines) 3-3. Oxidation of ethers 3-4. Oxidation of enols: α-Aminooxygenation of carbonyl compounds and further applications 3-5. Oxidation of alkenes 3-6. Oxidation of aromatic compounds 3-7. Oxidation of other substrates 3-8. Oxoammonium species for single electron oxidation 3-9. Oxoammonium species as a Lewis acids Conclusions and outlookThis paper is dedicated to Prof. Somsak Ruchirawat on the occasion of his 80th birthday.

show abstract

“…A recent review regarding the biocatalytic synthesis of bioactive compounds by laccases was written by Kudanga et al [82], and previously, a thorough review of laccase applications in organic synthesis was presented by Mogharabi and Faramarzi [83]. Recent synthetic efforts include the direct synthesis of furans from aliphatic diallyl ethers through a chemoenzymatic metathesis/aromatization cascade [84], the oxidation of 4-hydroxy-chalcones [85,86], the coupling of coumarins with acetone [87], the whole-cell catalyzed oxidation of 1,4-dihydropyridines [88], a sustainable iodination of phenols [89], the coupling of 4-phenylurazole with a number of aromatic compounds [90], the synthesis of triaminated cyclohexa-2,4-dienones from catechol [91], the synthesis of ferulic acid and ethyl ferulate derivatives [92], hydroxycinnamoyl peptides from ferulic acid and carnosine [93], coumestan derivatives [94], iodinated phenolic compounds [95], caffeic acid dimers [96], ferulic, sinapic, coumaric acid, and -OH dilignol dimers [97], and the oxidation of thioethers to sulfoxides [98]. In WO 2016050988A1, a chemoenzymatic preparation of biphenyl compounds by oxidative coupling is described, and similarly, a synthesis of binaphthyl compounds was reported in CN101418321A.…”

Section: Biocatalysismentioning

confidence: 99%

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

et al. 2019

View full text Add to dashboard Cite

There is a high number of well characterized, commercially available laccases with different redox potentials and low substrate specificity, which in turn makes them attractive for a vast array of biotechnological applications. Laccases operate as batteries, storing electrons from individual substrate oxidation reactions to reduce molecular oxygen, releasing water as the only by-product. Due to society’s increasing environmental awareness and the global intensification of bio-based economies, the biotechnological industry is also expanding. Enzymes such as laccases are seen as a better alternative for use in the wood, paper, textile, and food industries, and they are being applied as biocatalysts, biosensors, and biofuel cells. Almost 140 years from the first description of laccase, industrial implementations of these enzymes still remain scarce in comparison to their potential, which is mostly due to high production costs and the limited control of the enzymatic reaction side product(s). This review summarizes the laccase applications in the last decade, focusing on the published patents during this period.

show abstract

Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles

Cited by 41 publications

References 56 publications

Construction of Chemoenzymatic Linear Cascades for the Synthesis of Chiral Compounds

Construction of Chemoenzymatic Linear Cascades for the Synthesis of Chiral Compounds

The Utility of Oxoammonium Species in Organic Synthesis: Beyond Alcohol Oxidation

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

Contact Info

Product

Resources

About