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Jérôme Waser

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Publications associées (189)

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Jérôme Waser, Maria Victoria Vita, Paola Caramenti

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladiumcatalyzed decarboxylative allylation of alpha-azido and cyano beta-ketoesters is reported. Indano ...

American Chemical Society2015

One-Pot, Three-Component Arylalkynyl Sulfone Synthesis

Jérôme Waser, Chia-Chun Chen

A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO.SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A br ...

2015

Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents

Jérôme Waser, Chao Wang, Reto Frei, Durga Prasada Rao Hari

In this study, we present a highly efficient method for proteomic profiling of cysteine residues in complex proteomes and in living cells. Our method is based on alkynylation of cysteines in complex proteomes using a clickable alkynyl benziodoxolone bearin ...

Wiley-Blackwell2015

[4+2]-Annulations of Aminocyclobutanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Sophie Lucie Racine, Jérémy Vuilleumier, Daniele Perrotta

The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using sc ...

American Chemical Society2015

Taming Hypervalent Bonds and Strained Rings for Catalysis and Synthesis

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Sophie Lucie Racine, Maria Victoria Vita, Yifan Li, Reto Frei, Eloísa Sofía Serrano Robledo

Improving the synthesis of complex organic molecules is essential for progress in many fields such as medicine, agrochemicals or materials. Since 2007, our laboratory has been focusing on the development of non-classical bond disconnections based on the us ...

2014

Enantioselective Synthesis of Polycyclic Carbocycles via an Alkynylation-Allylation-Cyclization Strategy

Jérôme Waser, Pascal Miéville, Maria Victoria Vita

A new general three-stage strategy to access polycyclic ring systems bearing all-carbon quaternary centers with high enantioselectivity is reported. The required starting materials were readily accessed in racemic form through the alpha-alkynylation of ket ...

American Chemical Society2014

Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Eloísa Sofía Serrano Robledo

In this Letter, we describe the synthesis of new donor-acceptor substituted cyclopropanes bearing various imido groups and their use in [3+2]-annulation reactions. A sequence of palladium-catalyzed vinylation and rhodium-catalyzed cyclopropanation gave acc ...

Georg Thieme Verlag2014

Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Eloísa Sofía Serrano Robledo, Daniele Perrotta

We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines ...

American Chemical Society2014

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

Jérôme Waser, Filippo De Simone, Fides Benfatti, Florian Patrick Marie Daniel De la Barre De Nanteuil, Reto Frei, Eloísa Sofía Serrano Robledo

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subcl ...

Royal Society of Chemistry2014

Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism

Matthew Wodrich, Jérôme Waser, Reto Frei, Durga Prasada Rao Hari

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with ...

2014

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents

Jérôme Waser, Chia-Chun Chen

Highly efficient protocols for the alkynylation of H-phosphi(na)tes and secondary phosphine oxides with silyl, aryl and alkyl ethynyl-benziodoxolone (EBX) reagents are reported. Alkynyl phosphorus compounds were obtained in 69-93% yield without the need fo ...

Royal Society of Chemistry2014

Synthesis of (Carbo) nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Sophie Lucie Racine, Eloísa Sofía Serrano Robledo

(Carbo) nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-accep ...

Wiley-Blackwell2014

Gold-Catalyzed Regioselective Synthesis of 2- and 3-Alkynyl Furans

Jérôme Waser, Jonathan Brand, Yifan Li

Wiley-VCH Verlag GmbH2013

Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes

Raha Sedigh-Zadeh, Jérôme Waser, Stefano Nicolai

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this ...

American Chemical Society2013

A Highly Chemoselective and Practical Alkynylation of Thiols

Jérôme Waser, Reto Frei

A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagen ...

American Chemical Society2013

Zinc-gold cooperative catalysis for the direct alkynylation of benzofurans

Jérôme Waser, Yifan Li

The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. H ...

2013

C2-Selective Direct Alkynylation of Indoles

Stephanie Ganss, Jérôme Waser, Jonathan Brand, Gergely Laszlo Tolnai

The first C2-selective alkynylation of indoles using the hypervalent iodine reagent triisopropylsilylethyny1-1,2-benziodoxol-3(1H)-one (TIPS-EBX) with Pd(II) as a catalyst is described. This convenient and robust method gives a single-step access to substi ...

American Chemical Society2013

Gold-Catalyzed Alkynylation: Acetylene-Transfer instead of Functionalization

Jérôme Waser, Jonathan Brand, Yifan Li

Over the last fifteen years, gold has been raised from the status of an inert noble metal to one of the most-often-used catalysts in synthetic chemistry. The functionalization of the triple bond of alkynes has been especially successful in this respect. In ...

Wiley-V C H Verlag Gmbh2013

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

Davinia Fernández González, Jérôme Waser, Jonathan Brand

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

Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil

Wiley-Blackwell2013

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