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

Catalytic Enantioselective Synthesis of Inherently Chiral Macrocycles by Dynamic Kinetic Resolution

Kinetically fast racemization of chiral substrates through an achiral intermediate and enantioselective functionalization of one of the enantiomeric substrates forms the basis of the dynamic kinetic resolution (DKR) of centrally chiral molecules. We report ...

2024

Design and Synthesis of C4‐Symmetric Axially Chiral β‐Aryl Porphyrins and Application for Supporting Ir(III)‐Catalyzed Enantioselective C−H Alkylation

Jieping Zhu

A hitherto unknown class of C4-symmetric Caryl Cβ (C3, C8, C13, C18) axially chiral porphyrins has been synthesized and the application of their iridium (Ir) complexes in catalytic asymmetric C(sp3) H functionalization is documented. Cyclotetramerization o ...

Wiley-VCH Verlag GmbH2024

Chalcogen bonding catalysis

Jieping Zhu

Catalysts play a major role in chemical synthesis, and catalysis is considered to be a green and economic process. Catalysis is dominated by covalent interactions between the catalyst and substrate. The design of non-covalent catalysts came into limelight ...

Royal Society of Chemistry2024

Benchmarking machine-readable vectors of chemical reactions on computed activation barriers

Anne-Clémence Corminboeuf, Yannick Calvino Alonso, Puck Elisabeth van Gerwen, Ksenia Briling, Malte Martin Franke

In recent years, there has been a surge of interest in predicting computed activation barriers, to enable the acceleration of the automated exploration of reaction networks. Consequently, various predictive approaches have emerged, ranging from graph-based ...

Royal Soc 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

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

Switching the on-surface orientation of oxygen-functionalized helicene

Karl-Heinz Ernst, Christian Wäckerlin, Jan Voigt

Helicenes represent an important class of chiral organic material with promising optoelectronic properties. Hence, functionalization of surfaces with helicenes is a key step toward new organic materials devices. The deposition of a heterohelicene containin ...

Wiley2024

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

Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines**

Jérôme Waser, Nieves Pilar Ramirez Hernandez

An asymmetric 3-component reaction between EthynylBenziodoXoles (EBXs), 2,2,2-trifluorodiazoethane and nucleophiles catalyzed by a CuI-BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and a ...

Wiley-VCH Verlag GmbH2023

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Jieping Zhu, Hua Wu, Yuping He

An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of α,α-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitro- gen shift/1,2-aryl or alkyl migration sequence, ...

Wiley-VCH 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

Nanomole-scale photochemical thiol-ene chemistry for high-throughput late-stage diversification of peptide macrocycles

Mischa Schüttel, Alexander Lund Nielsen, Mark Daniel Nolan

The photochemical thiol-ene reaction is an efficient method for rapid and chemoselective formation of thioether linkages under mild conditions. It has found widespread use in small-molecule synthesis as well as peptide and protein chemistry. While high-thr ...

WILEY2023

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

Bayesian Optimization for Chemical Reactions

Philippe Schwaller, Bojana Rankovic, Jeff Guo

Reaction optimization is challenging and traditionally delegated to domain experts who iteratively pro-pose increasingly optimal experiments. Problematically, the reaction landscape is complex and often requires hundreds of experiments to reach convergence ...

Swiss Chemical Soc2023

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

CO2 Capture and Release in Amine Solutions: To What Extent Can Molecular Simulations Help Understand the Trends?

Wanda Andreoni, Fabio Pietrucci, Changru Ma

Absorption in amine solutions is a well-established advanced technology for CO2 capture. However, the fundamental aspects of the chemical reactions occurring in solution still appear to be unclear. Our previous investigation of aqueous monoethanolamine (ME ...

2023

Inferring free-energy barriers and kinetic rates from molecular dynamics via underdamped Langevin models

Fabio Pietrucci, Sara Bonella, David Daniel Girardier

Rare events include many of the most interesting transformation processes in condensed matter, from phase transitions to biomolecular conformational changes to chemical reactions. Access to the corresponding mechanisms, free-energy landscapes and kinetic r ...

Aip Publishing2023

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Srikrishna Bera, Chao Fan

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

2022

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

(4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Jérôme Waser, Stefano Nicolai

Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) ...

Wiley-VCH Verlag GmbH2022