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Concept

Aldolisation

Publications associées (32)

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023

Tandem Hydroformylation-Aldol Condensation Reaction Enabled by Zn-MOF-74

Berend Smit, Daniele Ongari

The tandem hydroformylation-aldol condensation (tandem HF-AC) reaction offers an efficient synthetic route to the synthesis of industrially relevant products. The addition of Zn-MOF-74 to the cobalt-catalyzed hydroformylation of 1-hexene enables tandem HF- ...

WILEY-V C H VERLAG GMBH2023

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Rémi Hugo Lavernhe

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

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

Chemodivergent Asymmetric Synthesis via Catalytically Formed Chiral Auxiliary

Mikus Purins

In summary, the development of the catalytically formed chiral auxiliary concept is described. In this approach, an oxazolidine auxiliary is installed via enantioselective Pd catalysis from readily available starting materials in an enantioselective tether ...

EPFL2023

Synthesis of metal oxide-overcoated carbon materials by liquid phase ALD and their applications in catalysis

Farzaneh Talebkeikhah

Coating nano particles and other substrates for efficiency enhancement, protection and obtaining new atomic structures is a widespread research topic in catalysis and material synthesis. Thus far, different approaches of coating, ranging from simplest to s ...

EPFL2023

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

Wiley-VCH Verlag GmbH2022

Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst

Jieping Zhu, Qiang Wang, Rémi Julien Sylvain Andres

The asymmetric Pictet–Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far-less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α-ketoamid ...

Wiley-VCH Verlag GmbH2022

Asymmetric Total Synthesis of Indole Alkaloids (+)-Condyfoline, (-)-Tubifoline, (+)-Dasycarpidone and (+)-Uleine

Bastien Delayre

The development of a titanium(III)-mediated cascade electrocyclisation/rearrangement for the enantioselective total synthesis of indole alkaloids (+)-condyfoline and (-)-tubifoline serve as the basis of the first chapter of this thesis. An introduction wil ...

EPFL2022

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

An Oculus to Profile and Probe Target Engagement In Vivo: How T-REX Was Born and Its Evolution into G-REX

Yimon Aye, Chloé Rogg

Here we provide a personal account of innovation and design principles underpinning a method to interrogate precision electrophile signaling that has come to be known as "REX technologies". This Account is framed in the context of trying to improve methods ...

American Chemical Society2021

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

Fluorene-based enamines as low-cost and dopant-free hole transporting materials for high performance and stable perovskite solar cells

Mohammad Khaja Nazeeruddin, Kasparas Rakstys, Albertus Adrian Sutanto, Maria Cristina Momblona Rincón

The power conversion efficiency of perovskite solar cells is approaching the Shockley-Queisser limit, and therefore this technology is next to the commercialization stage. Inexpensive and stable hole transporting materials are highly desirable for the succ ...

Royal Society of Chemistry2021

Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces

Harald Brune, Samuel Thomas Stolz

Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. In this study, we address this issue by using structurally co ...

NATURE RESEARCH2021

Atomic Level Insights of Non-Noble Metal Catalysts for the Oxygen Evolution Reaction

Lichen Bai

The conversion of intermittent renewable energy resources in the form of chemical bond, such as hydrogen production from electrochemical water splitting, is a promising way to satisfy the future global energy demand and address the environmental issues. Th ...

EPFL2021

Construction of Functional Superhydrophobic Biochars as Hydrogen Transfer Catalysts for Dehydrogenation of N-Heterocycles

Zhaowen Dong

To endow metal-free materials with the high catalytic activity that is typically featured by a metal-based catalyst is yet a constant pursuit in the field of catalytic chemistry. In this work, novel functional biochars (DCNs) were prepared from wheat straw ...

AMER CHEMICAL SOC2021

A computational workflow for the expansion of heterologous biosynthetic pathways to natural product derivatives

Vassily Hatzimanikatis, Jasmin Maria Hafner

Plant natural products (PNPs) and their derivatives are important but underexplored sources of pharmaceutical molecules. To access this untapped potential, the reconstitution of heterologous PNP biosynthesis pathways in engineered microbes provides a valua ...

Nature Research2021

Copper-catalyzed transformations of carboradicals generated by electrochemical and photochemical methods: oxidative amination and polyfluoroarylation

Xiangli Yi

Organic radicals are highly active species that can undergo various transformations. Electrochemistry and photochemistry are efficient methods for the generation of these species of high energy, through single electron transfer processes under mild conditi ...

EPFL2021

Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)

Jérôme Waser, Stefano Nicolai, Bastian Antoine Rodolphe Claude Muriel, Mikus Purins, Ugo Jonathan Orcel, Luca Buzzetti, Phillip Gulliver Dominic Greenwood

This review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered met ...

2020

Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins, Phillip Gulliver Dominic Greenwood, Luca Buzzetti

Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity ...

2020