Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Ma, Xinghua; Liu, Xin; Yates, Patrick; Raverty, Warwick D.; Banwell, Martin G.; Ma, Chenxi; Willis, Anthony C.; Carr, P.D.

doi:10.1016/j.tet.2018.03.023

Cited by 13 publications

(7 citation statements)

References 27 publications

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“…A few other examples of bio‐based molecules used as building blocks in polymer science have been described, which include itaconic acid, succinic acid, angelica lactone, levulinic acid, a precursor to methylene‐γ‐valerolactone, and levoglucosenone (LGO), a promising α,β‐unsaturated cyclic ketone (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters

et al. 2020

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The already‐reported, low‐yielding, and non‐sustainable Et3N‐mediated homocoupling of levoglucosenone (LGO) into the corresponding LGO‐CyreneTM diketone has been revisited and greened‐up. The use of methanol as both a renewable solvent and catalyst and K2CO3 as a safe inorganic base improved the reaction significantly with regards to yield, purification, and green aspects. LGO‐CyreneTM was then subjected to a one‐pot, H2O2‐mediated Baeyer–Villiger oxidation/rearrangement followed by an acidic hydrolysis to produce a new sterically hindered bicyclic monomer, 2H‐HBO‐HBO. This diol was further polymerized in bulk with diacyl chlorides to access new promising renewable polyesters that exhibit glass transition temperatures (Tg) from −1 to 81 °C and a good thermostability with a temperature at which 50 % of the mass is lost (Td50 %) of 349–406 °C.

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Section: Introductionmentioning

confidence: 99%

Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters

et al. 2020

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“…Its structural characteristics enable its use as a chiral template for the synthesis of natural and unnatural chemicals. The pseudoenantiomer isolevoglucosenone is also readily derived from LGO and used likewise. , LGO works as a scaffold for drug discovery, and its derivatives have shown anticancer, antitumor, and antimicrobial activities. ,− A controlled oxidation of LGO produces rare sugars that are not found in nature . The chemicals synthesized from LGO have been used for other purposes, including catalysts, ligands, and auxiliaries .…”

Section: Introductionmentioning

confidence: 99%

“…The pseudoenantiomer isolevoglucosenone is also readily derived from LGO and used likewise. 8,9 LGO works as a scaffold for drug discovery, and its derivatives have shown anticancer, antitumor, and antimicrobial activities. 7,10−15 A controlled oxidation of LGO produces rare sugars that are not found in nature.…”

Section: ■ Introductionmentioning

confidence: 99%

Catalytic Strategies for Levoglucosenone Production by Pyrolysis of Cellulose and Lignocellulosic Biomass

Kudo¹,

Huang

Asano³

et al. 2021

Energy Fuels

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Levoglucosenone (LGO) is a biobased compound that is generated during the pyrolysis of cellulose under catalysis. After several decades of foundational research into production methods, the relatively large-scale industrial production of LGO recently commenced. As a result, research on the application of LGO has increased and extended to the production of commodity chemicals, such as solvents, polymers, resins, and fuels, with LGO as the feedstock, while seeking to minimize production costs. An analysis and summary of previous achievements can help to inform the development of better production methods. We found that existing production methods can be organized into three categories depending on the strategies for exploiting catalysis. This minireview summarizes advances in the technologies used to produce LGO based on each catalytic strategy and recommends possible directions for future research by drawing on knowledge synthesized from the database.

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“…Furthermore, the hydrogenated derivative Cyrene (dihydrolevoglucosenone) has entered the marketplace as a less toxic replacement for the industrial solvent N -methylpyrrolidone (NMP) . Our ongoing interest , in the identification and exploitation of cellulose- and chitin-derived platform molecules for a range of purposes prompted us to explore ways in which levoglucosenone ( 2 ) and its readily derivable pseudoenantiomer isolevoglucosenone (isoLGO, 3 ) could be used in the development of more sustainably produced polymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale

et al. 2020

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The commercially available, abundant and homochiral cellulose pyrolysis product levoglucosenone (LGO) together with the readily derived isolevoglucosenone (isoLGO) form, in a stereoselective manner, Diels–Alder adducts with cyclopentadiene (CPD). These ring-fused norbornene systems, each of which incorporates six centers of chirality and is pseudoenantiomeric in nature, undergo ring-opening metathesis polymerization (ROMP) in the presence of a range of ruthenium-based catalysts to produce polymers embodying both carbo- and heterocyclic motifs. Under such conditions, controlled polymerizations take place with target molecular weights matching the theoretical ones and with low dispersities (from 1.1 to 1.4) normally being observed. Reduction of the carbonyl group in the Diels–Alder adduct derived from LGO provides the corresponding epimeric alcohols that can be etherified and the resulting ethers, including fluorine-containing ones, also yield well-controlled polymers via ROMP. This thus represents an efficient method for producing stereochemically and functionally diverse polymers from a renewable feedstock available at an industrial scale. These polymerizations are living ones as demonstrated by the facile preparation of block copolymers from the two Diels–Alder adducts.

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Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Cited by 13 publications

References 27 publications

Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters

Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters

Catalytic Strategies for Levoglucosenone Production by Pyrolysis of Cellulose and Lignocellulosic Biomass

Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale

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