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Concept

Réaction de Wittig

Publications associées (19)

Horner-Wadsworth-Emmons olefination for bioconjugation

Yimon Aye

Through site-specific generation of intermediary reactive aldehydes, Horner-Wadsworth-Emmons olefination can now deliver selective functionalization of stable recombinant proteins and monoclonal antibodies, whilst preserving protein integrity. ...

Springernature2024

Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Jieping Zhu, Anne-Clémence Corminboeuf, Qian Wang, Simone Gallarati, Takuji Fujii

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

Synthesis of 3-Acyloxyindolenines by TiCl3-Mediated Reductive Cyclization of 2-(ortho-Nitroaryl)-Substituted Enol Esters

Qian Wang, Jieping Zhu, Cyril Piemontesi, Dina Boyarskaya

In the presence of TiCl3, the reductive cyclization of tetrasubstituted enol esters bearing a 2-(ortho-nitroaryl) substituent affords 3-acyloxy-2,3-disubstituted indolenines in good yields. A domino process involving the partial reduction of nitro to a nit ...

2022

Copper-Catalyzed Cyanoalkylative Aziridination of N-Sulfonyl Allylamines

Jieping Zhu, Qian Wang, Minh Tu Ha, Weisi Guo

Reaction of N-arylsulfonyl allylamines with alkyl nitriles in the presence of di-tert-butyl peroxide (DTBP) and a catalytic amount of copper salt afforded homologated aziridines in 43-86% yield. A sequence involving addition of the in situ generated cyanom ...

Wiley2020

Identifying Reaction Species by Evolutionary Fitting and Kinetic Analysis: An Example of CO2 Hydrogenation in DRIFTS

Andreas Züttel, Ligang Wang, Kun Zhao, Emanuele Moioli, Marco Calizzi

Diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS) investigations of molecules at the surface of catalysts exhibit a strong overlap of the adsorption peaks. Therefore, the investigation of the CO2 hydrogenation on a highly active catalyst ...

2019

Silver Nitrate-Catalyzed Isocyanide Insertion/Lactamization Sequence to Imidazolones and Quinazolin-4-ones: Development and Application in Natural Product Synthesis

Jieping Zhu, Qian Wang, Antonin François Roland Clemenceau

Silver nitrate-catalyzed reaction of methyl α,α-disubstituted α-isocyanoacetates with primary amines afforded 3,5,5-trisubstituted imidazolones in good to excellent yields. A silver salt-catalyzed insertion of the isocyano group into the N−H bond of the am ...

American Chemical Society2017

Chiral Cyclopentadienyl Ruthenium (II) Complexes : Synthesis and Applications in Catalysis

David Kossler

Cyclopentadienyl ruthenium(II) complexes are an important class of homogenous catalysts. They engage in a multitude of different transformations, for example cycloisomerizations. Due to a lack of suitable chiral cyclopentadienyl ligands, no efficient enant ...

EPFL2017

Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

Jieping Zhu, Qian Wang, Ala Bunescu, Minh Tu Ha

A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded gamma-azido alkyl nitriles by formation of one C(sp3)-C(sp3) bond and one C(sp3)-N bond. The transformation allows concomitant introduction of two highly versat ...

Wiley-Blackwell2017

Synthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile

Jieping Zhu, Qian Wang

The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehyde ...

American Chemical Society2016

Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B

Jieping Zhu

An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown’s enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner–Wadsworth– Emmons olefination, 3) Evans aldo ...

Wiley-Blackwell2015

Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles

Jieping Zhu, Qian Wang, Ala Bunescu

A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation ...

Amer Chemical Soc2015

Aromatic Homologation by Non- Chelate- Assisted RhIII- Catalyzed C -H Functionalization of Arenes with Alkynes

Nicolai Cramer, Van Manh Pham

Larger condensed arenes are of interest owing to their electro- and photochemical properties. An efficient synthesis is the catalyzed aromatic annulation of a smaller arene with two alkyne molecules. Besides difunctionalized starting materials, directed CH ...

Wiley-VCH Verlag GmbH2014

Controlled Formation of Mixed-Metal Macrocycles Using Dynamic Exchange Processes and Steric Constraints

Rosario Scopelliti, Kay Severin, Zacharias Immanuel Grote

The exchange reaction of the trinuclear macrocycles [(C6H3iPr3)Ru(C5H3NO2)]3 (AAA) and [(cymene)Ru(C5H3NO2)]3 (BBB) has been studied. It was found that the equilibration proceeds in two steps and that the final mixture is completely dominated by the mixed- ...

2007

Wittig rearrangement of lithiated allyl aryl ethers: a mechanistic study

A -75 DegC, alpha-lithiated allyl Ph ether undergoes mainly the Wittig rearrangement to afford, after acidic hydrolysis, 1-phenyl-2-propen-1-ol as the main product. A second metalation taking place at one of the ortho positions is the sole competing side r ...

2006

Embedding an Allylmetal Dimer in a Chiral Cavity: The Unprecedented Stereoselectivity of a Twofold Wittig [1,2]-Rearrangement

Frédéric Bailly

After alpha,alpha'-dimetalation, both 2,2'-diallyloxy-1,1'-binaphthyl and 2,2'-di-2-methylallyloxy-1,1'-binaphthyl undergo the Wittig rearrangement with perfect diastereoselectivity. When racemic 1,1'-binaphthyl-2,2'-diol ("BINOL") is used as the starting ...

2006

Synthesis of aza-C-disaccharides (dideoxyimino-alditols C-linked to monosaccharides) and analogues

Pierre Vogel

The first aza-C-disaccharide (D-azaMan-beta-CHz-(1 -> 6)-D-Man-alpha-OMe) that mimicks alpha-D-Manp-(1 -> 6)-alpha-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are ...

Georg Thieme Verlag2005

The synthesis and characterisation of bis(phosphane)-linked (eta(6)-p-cymene)ruthenium(II)-borane compounds

Paul Joseph Dyson, Rosario Scopelliti

The reaction of [(η6-p-cymene)RuCl2]2 with some bis(phosphane) ligands (dppm, dppe, dppv, dppa, dpp14b, dppf) has been investigated. In general mixtures of products were obtained, although the pendant phosphane complexes [( ...

2005

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

Buttressing effects responsible for the meta-deprotonation of trialkylsilyl-substituted haloarenes by organometallic reagents : an unprecedented phenomenon

Christophe Heiss

(2,6-Dichlorophenyl)trimethyl- and triethylsilane exhibit untypical reactivity patterns toward strong bases: when treated at -100 °C with lithium 2,2,6,6-tetramethylpiperidide two, with sec- or tert-butyllithium even three organometallic intermediates are ...

EPFL2005