Publications related to Acetal

Development of Sustainable Carbohydrate-Based Solvents by Acetal Functionalisation of Biomass

Organic solvents are ubiquitous in industrial and domestic applications from the production of pharmaceuticals to household consumer products. The negative impact of most traditional solvents, especially aprotic types, on the environment, health, and safet ...

EPFL2024

Formaldehyde regulates one-carbon metabolism and epigenetics

Yimon Aye

Recently, Pham et al. used an array of model systems to uncover a role for the enzyme methionine adenosyltransferase (MAT) -1A, which is mainly expressed in liver, in both sensing formaldehyde and regulating transcriptional responses that protect against i ...

Cell Press2024

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

Extraction and controlled functionalization of lignin for materials applications

Stefania Bertella

Lignin is a renewable aromatic polymer that due to its abundance and unique chemical structure is a promising candidate to replace aromatic materials that are currently sourced from fossil oil. The same structure of lignin poses however drawbacks for its v ...

EPFL2022

Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

Jérôme Waser, Eliott Hugo Joran Le Du, Marion Marie-Agnès Garreau

A photoredox-catalyzed oxidative decarboxylative coupling of small peptides is reported, giving access to a variety of N,O-acetals. They were used as intermediates for the addition of phenols and indoles, leading to novel peptide scaffolds and bioconjugate ...

2021

Diformylxylose as a new polar aprotic solvent produced from renewable biomass

Jeremy Luterbacher, Anastasiia Komarova, Graham Reid Dick

Lignin is a promising candidate for the replacement of fossil-based materials, due to its natural abundance and aromatic structure. This same structure poses major challenges to lignin's exploitation for material development. The harsh conditions generally ...

2021

Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Matthew Wodrich, Eliott Hugo Joran Le Du

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis of ...

2021

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the gamma or delta po ...

Wiley-VCH Verlag GmbH2020

Development of Photocatalysts towards the Visible-Light driven C-Terminal Bioconjugation of Peptides and Proteins

Marion Marie-Agnès Garreau

If small molecules have led to tremendous progress in curing diseases, new therapeutic agents such as peptides or antibody-drugs conjugates have emerged as a highly promising next generation of pharmaceuticals. As for small molecules, their derivatization ...

EPFL2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal ca ...

Wiley-VCH Verlag GmbH2019

Production, characterization and upgrading of biomass-derived acetal-stabilized carbohydrates

Ydna Marie Questell-Santiago

Biomass is an attractive source of renewable carbon-based fuels and chemicals. Multiple research efforts are centered around integrated biorefineries, where all fractions of biomass are converted to fuels or chemical products. These efforts are focused aro ...

EPFL2019

Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Nicolai Cramer, Daria Grosheva

Asymmetric metal-catalyzed C-H functionalization is a powerful strategy for the rapid generation of complex target molecules from simple precursors. While aryl (pseudo) halides have been used as electrophilic substrates in enantioselective Pd(0)-catalyzed ...

2019

Carbohydrate stabilization extends the kinetic limits of chemical polysaccharide depolymerization

Jeremy Luterbacher, Masoud Talebi Amiri, Ydna Marie Questell-Santiago, Raquel Zambrano Varela

Polysaccharide depolymerization is an essential step for valorizing lignocellulosic biomass. In inexpensive systems such as pure water or dilute acid mixtures, carbohydrate monomer degradation rates exceed hemicellulose—and especially cellulose—depolymeriz ...

2018

In Situ Tethering Strategies for the 3-Component Synthesis of Vicinal Amino Alcohols and Diamines via Pd-Catalyzed Carboetherification and Carboamination

Ugo Jonathan Orcel

Vicinal amino alcohols and diamines are privileged motifs in organic chemistry. As such, they have been targets of choice for exploring and developing novel and more efficient strategies in organic synthesis. In this context, the difunctionalization of ole ...

EPFL2017

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination

Jérôme Waser, Ugo Jonathan Orcel

A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formatio ...

Wiley-VCH Verlag GmbH2016

Palladium-Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification

Jérôme Waser, Ugo Jonathan Orcel

Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and ...

Wiley-Blackwell2015

One-Pot, Three-Component Arylalkynyl Sulfone Synthesis

Jérôme Waser, Chia-Chun Chen

A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO.SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A br ...

2015

Acetal-Functionalized RAPTA Complexes for Conjugation and Labeling

Paul Joseph Dyson, Wee Han Ang

Ruthenium-arene complexes bearing the 1,3,5-triaza-7-phosphatricyclo-[3.3.1.1]decane ligand, namely, RAPTA compounds, are widely investigated as potential antimetastatic agents for cancer therapy. Although much evidence points toward covalent binding with ...

American Chemical Society2011