Publications related to Enantioselective Access to 1H-Isoindoles with Quaternary Stereogenic Centers by Palladium(0)-Catalyzed C-H Functionalization

Related publications (20)

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

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

Yi Zhang, Nicolai Cramer, Shouguo Wang

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

Enantioselective Total Synthesis of (+)-Stephadiamine

Qian Wang, Jieping Zhu, Guang Li, Baochao Yang

An asymmetric synthesis of (+)-stephadiamine has been accomplished featuring (a) an enantioselective dearomatizative Michael addition to generate a quaternary stereocenter; (b) a domino sequence involving reductive generation of nitrone from γ-nitro ketone ...

2023

Rapid, Selective Extraction of Silver from Complex Water Matrices with a Metal-Organic Framework/Oligomer Composite Constructed via Supercritical CO2

Wendy Lee Queen

Every year vast quantities of silver are lost in various waste streams; this, combined with its limited, diminishing supply and rising demand, makes silver recovery of increasing importance. Thus, herein, we report a controllable, green process to produce ...

Wiley-VCH Verlag GmbH2023

Tetracycline derivative induced mitohormesis mediates disease tolerance against viral infections

Johan Auwerx, Adrienne Joëlle Laurence Mottis

The present invention relates to a compound of formula (I) or formula (II) formula (I) formula (II) or a salt thereof for use in treating or preventing a viral disease or viral infection, wherein within formula (I) or (II) (A) A is H or OH, X is CH3, and R ...

2023

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

Enantioselective Total Synthesis of (+)-Alstilobanine C, (+)-Undulifoline, and (-)-Alpneumine H

Qian Wang, Jieping Zhu, Cyril Piemontesi, Guang Li, Nicolas David Gaeng

We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

Wiley-VCH Verlag GmbH2021

Use of sultines in the asymmetric synthesis of polypropionate antibiotics

Pierre Vogel, Maris Turks, Laure Bouchez, Cotinica Craita, Xiaogen Huang, Freddy Fonquerne

At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 degrees C and equilibrate with the more stable 2,5- ...

De Gruyter2008

Le réarrangement [1,2] de Wittig : contribution à l'étude de son mécanisme et de ses applications

Frédéric Bailly

The importance of catalysis in chemistry has not to be proved anymore. Be it homogeneous or heterogeneous catalysis, the constant progresses observed in that field proves its obvious interest. The asymmetric homogeneous catalysis is a method of choice to s ...

EPFL2005

Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity

Farzaneh Fadaei Tirani, Kurt Schenk

The bidentate carboxamide ligand N-(thiazole-2-yl) picolinamide (LH) was synthesized in the environmentally friendly ionic liquid TBAB, and the five-coordinated Cu-II-complex, [Cu(L)(2)(H2O)]center dot CHCl3 (1) was synthesized from LH and copper(II)acetat ...

2020

A recyclable metal-organic framework for ammonia vapour adsorption

Kyriakos Stylianou, Ngoc Tú Nguyên

Herein, we present a new strategy to design metal-organic frameworks (MOFs) as adsorbents for ammonia (NH3) vapour. The linking ligand is functionalized with a sterically hindered Lewis acidic boron (B) centre, allowing efficient capture of NH3 and easy re ...

Royal Society of Chemistry2020

Development of Catalytic Asymmetric C-H Functionalizations with Chiral Cyclopentadienyl Iridium(III) Complexes

Yun-Suk Jang

Cp*Ir(III) catalyzed C-H functionalization is a growing field, since it provides novel complementary reactivities, but enantioselective C-H functionalization reactions with this metal remain a niche. This thesis investigates CpXIr(III) catalyzed asymmetric ...

EPFL2019

Indole Alkaloids, Macrocycles and Heterocycles : Interplay between Methodological Development and Total Synthesis

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

Pd(0)-Catalysed C-H Functionalisations for the Enantioselective Synthesis of N-Heterocycles

Julia Pedroni

Transition-metal catalysed enantioselective Câ H functionalisations enable rapid increase of molecular complexity via non-classical disconnections. This thesis describes the development of intramolecular Pd(0)-catalysed C-H functionalisations for the asym ...

EPFL2017

"Divergent Total Synthesis of (-)-Rhazinilam, (-)-Leucomidine B and (+)-Leuconodine F" and "Synthetic Studies Towards Sarpagine-Related Indoles"

Dylan Jean Robert Dagoneau

The work presented in this thesis focuses on the synthesis of monoterpene indole alkaloids. The first part describes the divergent total synthesis of (-)-rhazinilam, (-)-leucomidine B and (+)-leuconodine F, three structurally distinct natural products of t ...

EPFL2017

Ni-based structured catalyst for selective 3-phase hydrogenation of nitroaromatics

Paul Joseph Dyson, Lioubov Kiwi, Thomas La Grange, Daniel André Samuel Lamey, Oliver Anthony Beswick

We report herein on the development of Ni-based catalyst using activated carbon fibres (ACFs) as a structured support and its application for the three‐phase hydrogenation of nitroarenes (T = 353 K; P = 10 bar). It was shown that metallic Ni0 nanoparticles ...

Elsevier2016

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates

Jérôme Waser, Jonathan Brand, Davinia Fernández González

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scanning ...

Wiley-Blackwell2013

Catalytic Formal Homo-Nazarov Reaction and Other Cyclizations of Cyclopropanes : from Methodology to Total Synthesis

Filippo De Simone

The increasing progress in medicinal chemistry and chemical biology requires more versatile synthetic strategies for the generation of libraries of active compounds and theirs analogues. A wide range of biologically active natural and synthetic compounds c ...

EPFL2012

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes

Jérôme Waser, Fides Benfatti, Tanguy Jean Daniel Saget, Filippo De Simone

The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization ...

2011

Total asymmetric synthesis of glycomimetics and polypropionates of biological interest

Pierre Vogel

Using readily available chiral auxiliaries such as (+)- and (-)-camphanic acid, (R,R)- and (S,S)-tartaric acid derivatives (e.g. RADO(R)-COCl, SADO(R)-COCl) efficient diastereoselective syntheses of rare sugars and glycomimetics have been developed. They e ...

2008