Publications associées à Ring-closing metathesis

Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Jérôme Waser, Matthew Wodrich, André Bossonnet

We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

2023

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

Iron-Catalyzed Reductive Coupling of Alkyl Iodides with Alkynes To Yield cis-Olefins: Mechanistic Insights from Computation

Xile Hu

In a recent study, a new procedure for Z-selective olefin synthesis by reductive coupling of alkyl iodides with terminal alkynes in the presence of iron salts is described. This transformation is representative of many newly developed synthetic routes thro ...

AMER CHEMICAL SOC2020

Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition

Xile Hu, Alexis Baptiste Cheseaux, Guido Barzanò

Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stere ...

2019

Predicting Product Distribution of Propene Dimerization in Nanoporous Materials

Berend Smit

In this work, a theoretical framework is developed to explain and predict changes in the product distribution of the propene dimerization reaction, which yields a mixture of C-6 olefin isomers, resulting from the use of different porous materials as cataly ...

American Chemical Society2017

Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes

Xile Hu, Chi Wai Cheung, Fedor Zhurkin

Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes. The method employs inexpensive an ...

American Chemical Society2015

Highly Enantioselective Rhodium(I)-Catalyzed Carbonyl Carboacylations Initiated by C-C Bond Activation

Nicolai Cramer, Laetitia Marie Mélanie Souillart

The lactone motif is ubiquitous in natural products and pharmaceuticals. The Tishchenko disproportionation of two aldehydes, a carbonyl hydroacylation, is an efficient and atom-economic access to lactones. However, these reaction types are limited to the t ...

Wiley-Blackwell2014

Impact of organic-ligand shell on catalytic performance of colloidal Pd nanoparticles for alkyne gas-phase hydrogenation

Lioubov Kiwi, Fernando Cardenas Lizana, Daniel André Samuel Lamey, Irina Prokopyeva

Monodispersed Pd nanoparticles (NPs) have been prepared by colloidal technique and deposited on a structured support consisting of carbon nanofibers (CNF) grown on sintered metal fibres (SMF). The surface properties of Pd NPs have been fine-tuned by (i) ch ...

Elsevier2014

Bicyclic peptide ligands pulled out of cysteine-rich peptide libraries

Christian Heinis, Petr Leiman, Inmaculada Rentero Rebollo, Shiyu Chen, Jeremy Touati, Julia Morales Sanfrutos

Bicyclic peptide ligands were found to have good binding affinity and target specificity. However, the method applied to generate bicyclic ligands based on phage-peptide alkylation is technically complex and limits its application to specialized laboratori ...

2013

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Jérôme Waser, Filippo De Simone

The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with amin ...

2011

Ruthenium-Catalyzed Synthesis of 1,5-Dichlorides by Sequential Intermolecular Kharasch Reactions

Rosario Scopelliti, Kay Severin, Aurélien Godinat, Katrin Anne Thommes, Charlotte Buron

Sequential intermolecular atom transfer radical addition reactions of activated dichlorides Cl2CRR′ (R = CN, CO2Et, R′ = H, CN, CO2Et) with two olefins catalyzed by [Cp*RuCl2(PPh3)] in the presence Mg allow the synthesis of linear 1,5-dichlorides. Differen ...

Wiley-Blackwell2011

Synthesis of Optically Active 5-Alkoxy-6-methylcyclohex-2-en-1-ones and 4-Alkoxy-5-methylcyclopent-1-enyl Benzoate

Pierre Vogel, Maris Turks

The reaction of (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate with allyltrimethylsilane in SO,- and in the presence of a catalytic amount of Tf2NTMS gives a silyl sulfinate intermediate that furnishes (-)-(6Z,1'S,4S,5S)-5-methyl- ...

American Chemical Society2009

Chelating NHC Ruthenium(II) Complexes as Robust Homogeneous Hydrogenation Catalysts

Gabor Laurenczy, Antonia Neels

A series of ruthenium(II) N-heterocyclic carbene chelate complexes were prepd. by using bidentate chelating alkene-carbene, thioether-carbene, carboxylate-carbene and bis-carbene ligands. Metalation of 1-R-3-X-imidazolium salts (1-3, R = Me, X = allyl, MeS ...

2009