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Synthesis of C-glycosides and C-linked disaccharides through carbonylative Stille coupling reactions

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Publications associées (33)

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Combining multi-stage ion mobility spectrometry with cryogenic infrared spectroscopy for glycan analysis

Priyanka Bansal

Structural analysis of biomolecules is essential to understanding biological processes. Among the various classes of biomolecules, glycans have gained significant attention recently due to their ubiquitous roles in biological systems. However, study of gly ...

EPFL2022

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds

Ashis Kumar Das

Transition metal-catalyzed C-H activation is a powerful tool for the synthesis of organic building blocks, materials, and natural products. Over the last decade, directing-group-assisted metal-catalyzed C-H functionalization has attracted increasing intere ...

EPFL2022

A New Strategy Coupling Ion-Mobility-Selective CID and Cryogenic IR Spectroscopy to Identify Glycan Anomers

Thomas Rizzo, Ahmed Ben Faleh, Stephan Warnke, Eduardo Carrascosa Casado, Priyanka Bansal, Robert Paul Pellegrinelli, Lei Yue

Determining the primary structure of glycans remains challenging due to their isomeric complexity. While high-resolution ion mobility spectrometry (IMS) has recently allowed distinguishing between many glycan isomers, the arrival-time distributions (ATDs) ...

2022

Development of metal-organic frameworks based on N-heterocyclic ligands

Ilia Kochetygov

Metal-organic frameworks (MOFs) have firmly established in the field of porous materials since their early discovery in the 1990s. With a plethora of applications, these materials offer endless possibilities owing to their tunable, modular nature. The vast ...

EPFL2022

Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation

Jérôme Waser, Mikus Purins, Ashis Kumar Das, Luca Buzzetti

We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehydederived tether to build chiral oxazolidines. Diastereoselective hydrogenation using a heterogeneous palladium catalyst then gave acc ...

2022

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

Thomas Rossolini, Jérôme Waser, Stefano Nicolai, Ashis Kumar Das

A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturate ...

2022

Identification of Mobility-Resolved N-Glycan Isomers

Thomas Rizzo, Ahmed Ben Faleh, Stephan Warnke, Priyanka Bansal, Robert Paul Pellegrinelli

Glycan analysis has evolved considerably during the last decade. The advent of high-resolution ion-mobility spectrometry has enabled the separation of isomers with only the slightest of structural differences. However, the ability to separate such species ...

AMER CHEMICAL SOC2022

Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Jieping Zhu, Anne-Clémence Corminboeuf, Qian Wang, Simone Gallarati, Takuji Fujii

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

Warping-Inclusive Kinematic Coupling in Mixed-Dimension Macro Models for Steel Wide Flange Beam Columns

Dimitrios Lignos, Albano António De Abreu E Presa De Castro E Sousa, Alexander Riley Hartloper

A warping-inclusive kinematic coupling method to be used in finite-element analysis of members featuring wide-flange cross sections is proposed in this paper. This coupling method is used in mixed-dimension macromodels that combine continuum and beam-colum ...

2022

Oxidase-Type C-H/C-H Coupling Using an Isoquinoline-Derived Organic Photocatalyst

Xile Hu, Lei Zhang

Oxidase-type oxidation is an attractive strategy in organic synthesis due to the use of O-2 as the terminal oxidant. Organic photocatalysis can effect metal-free oxidase chemistry. Nevertheless, current methods are limited in reaction scope, possibly due t ...

Wiley-VCH Verlag GmbH2022

Catalytic enantioselective Pictet-Spengler reaction of carbonyl compounds: Development and application to the asymmetric total synthesis of indole alkaloids

Rémi Julien Sylvain Andres

This thesis consists in an extensive study about the enantioselective Pictet-Spengler reaction (EPSR) and its application to the total synthesis of monoterpene indole alkaloids (MIAs). The general introduction presents the literature background about this ...

EPFL2022

3PAC: A Plug-and-Play System for Distributed Power Sharing and Communication in Modular Robots

Jamie Paik, Christoph Heinrich Belke, Kevin Andrew Holdcroft

In modular robotics, there is classically a compromise between coupling complexity and functionality. The mechanical and electrical designs are linked, such that adding electrical features often requires redesigning the mechanical components. However, incr ...

IEEE-INST ELECTRICAL ELECTRONICS ENGINEERS INC2022

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021