Publications related to From Racemic to Enantioselective Total Synthesis of Trigonoliimines via Development of an Organocatalytic Enantioselective Michael Addition of α-Aryl-α-isocyanoacetate to Vinyl Phenyl Selenone

Recent advances in Rh(I)-catalyzed enantioselective C-H functionalization

Nicolai Cramer, Shouguo Wang, Yi Zhang, Zhen Chen

Chiral carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds are pervasive and very essential in natural products, bioactive molecules, and functional materials, and their catalytic construction has emerged as one of the hottest research fields in syntheti ...

Royal Society of Chemistry2024

New Applications of 1,3,2-Diazaphospholenes in Catalysis

Johannes Klett

The constant urge to construct new molecules in an economical and sustainable fashion led to the development of numerous metal-catalyzed transformations. Organocatalysts consisting of abundant and more sustainable elements offer an elegant solution to over ...

EPFL2024

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

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

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

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

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

Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces

Harald Brune, Roland Widmer, Roland Hany, Michael Bauer, 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

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

Qian Wang, Jieping Zhu, Bastien Delayre

The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new s ...

2021

Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Jieping Zhu, Shuo Tong

We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derive ...

2020

Exploiting the chirality of intermetallic PdGa

Samuel Thomas Stolz

The intermetallic compound PdGa has recently attracted considerable interest for combining high catalytic activity with high reaction selectivity in symmetric heterogeneous catalysis, in particular semi-hydrogenation of acetylene and methanol steam reformi ...

EPFL2020

Reactions of nitrogen-containing compounds with ozone: kinetics and mechanisms

Sung Eun Lim

Nitrogen-containing moieties are widespread in natural waters in dissolved organic nitrogen and micropollu-tants. They are often susceptible to an electrophilic attack of ozone because of the electron-rich nature of the neutral form of nitrogen in organic ...

EPFL2020

Mechanisms of the Heterogeneously Catalyzed Reaction of CO2 Hydrogenation on Transition Metal Surfaces

Kun Zhao

Renewable energy supply and energy storage in a closed materials cycle are the urgent global challenges of the 21st century. Carbon dioxide (CO2) hydrogenation over catalysts is a method to produce synthetic fuels from renewable energy in a CO2 neutral cyc ...

EPFL2020

Iridium-catalyzed acid-assisted asymmetric hydrogenation of oximes to hydroxylamines

Nicolai Cramer

Asymmetric hydrogenations are among the most practical methods for the synthesis of chiral building blocks at industrial scale. The selective reduction of an oxime to the corresponding chiral hydroxylamine derivative remains a challenging variant because o ...

American Association for the Advancement of Science2020

Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals

Guido Barzanò

C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...

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

CO2 chemical transformations using metal-organic frameworks

Serhii Shyshkanov

During the last decades, intensive efforts have been applied to tackle the enormous emissions of CO2 into atmosphere. These efforts include not only developing efficient carbon capture techniques, but also the introduction of new ways to transform the capt ...

EPFL2020

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2

Martin Hulla

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

EPFL2019