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Jérôme Waser

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Publications associées (189)

Azidation of beta-Keto Esters and Silyl Enol Ethers with a Benziodoxole Reagent

Jérôme Waser, Maria Victoria Vita

The efficient azidation of beta-keto esters and silyl enol ethers using a benziodoxole-derived azide transfer reagent is reported. The azidation of cyclic beta-keto esters could be achieved in up to quantitative yields in the absence of any catalyst. In th ...

American Chemical Society2013

Catalytic Friedel-Crafts Reaction of Aminocyclopropanes

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

A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups ...

American Chemical Society2013

Indole Alkaloids Synthesis via a Selective Cyclization of Aminocyclopropanes

Jérôme Waser, Filippo De Simone

The continuous progress in medicinal chemistry requires more versatile synthetic strategies for the generation of large libraries of active compounds and their analogues. As a result, the research for new effective cyclization and cycloaddition reactions i ...

2012

Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones

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

The first enantiospecific [3+2] annulation of D-A amino-cyclopropanes with ketones is reported herein (see scheme; Phth = phthaloyl). The reaction is catalyzed by 5 mol % of tin(IV) chloride at -78 °C and gives aminotetra-hydrofurans bearing a C5-quaternar ...

2012

Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines

Jérôme Waser, Jonathan Brand

A method for the para-selective alkynylation of anilines is reported using AuCl as catalyst and triisopropylsilylethynyl-1,2-benziodoxol-3(1H)-one (TIPS-EBX) as an electrophilic acetylene equivalent. Para-alkynyl anilines substituted at positions 2 or 3 we ...

American Chemical Society2012

Asymmetric Organocatalysis Meets Hypervalent Iodine Chemistry for the alpha-Functionalization of Carbonyl Compounds

Davinia Fernández González, Jérôme Waser, Fides Benfatti

Wiley-VCH Verlag2012

Electrophilic alkynylation: the dark side of acetylene chemistry

Jérôme Waser, Jonathan Brand

In addition to the well-established nucleophilic alkynylation, the use of electrophilic alkynes can expand tremendously the scope of acetylene transfer reactions. The use of metal catalysis has recently led to a rebirth of this research area. Halogenoalkyn ...

Royal Society of Chemistry2012

Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism

Rosario Scopelliti, Jérôme Waser, Jonathan Brand

This report describes a full study of the gold-catalyzed direct alkynylation of indoles, pyrroles, and thiophenes using alkynyl hypervalent iodine reagents, especially the study of the structural requirements of alkynyl benziodoxolones for an efficient ace ...

2012

Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans

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

The first method for the [3 + 2] annulation of donor acceptor aminocyclopropanes with aldehydes is reported. The reaction is catalyzed by iron trichlorlde on alumina in yields up to 99% and with excellent cis selectivities (up to >20:1) and represents a st ...

American Chemical Society2012

Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines

Jérôme Waser, Jonathan Brand

An efficient procedure was developed for the synthesis of 1-[(triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one on a 100-mmol (36-g) scale. The benziodoxolone can be used for the gold-catalyzed direct alkynylation of indole, 2-hexylthiophene, ...

2012

Cyclopropanes and Hypervalent Iodine Reagents: High Energy Compounds for Applications in Synthesis and Catalysis

Davinia Fernández González, Jérôme Waser, Filippo De Simone, Jonathan Brand, Stefano Nicolai

One of the major challenges faced by organic chemistry is the efficient synthesis of increasingly complex molecules. Since October 2007, the Laboratory of Catalysis and Organic Synthesis (LCSO) at EPFL has been working on the development of catalytic react ...

2011

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

Davinia Fernández González, Jérôme Waser, Jonathan Brand, Stefano Nicolai

In the last decades, hypervalent iodine reagents have raised from chemical curiosities to mainstream reagents in organic synthesis. The use of benziodoxole-derived reagents has been especially successful in oxidation methods, whereas non-cyclic iodinanes h ...

Royal Society of Chemistry2011

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

Jérôme Waser, Jonathan Brand

The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-su ...

2011

A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine

Jérôme Waser, Cyril Piemontesi, Stefano Nicolai

Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, ...

Wiley-VCH Verlag GmbH2011

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes

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

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

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

Davinia Fernández González, Jérôme Waser, Jonathan Brand, Stefano Nicolai

Royal Society of Chemistry2011

Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines

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

With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yield ...

Wiley-VCH Verlag GmbH2011

Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines

Jérôme Waser, Stefano Nicolai

The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of a ...

American Chemical Society2011

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

Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters

Davinia Fernández González, Jérôme Waser, Jonathan Brand

Hot alkyne! The in situ generation of Ethynyl-1,2-BenziodoXol-3(1H)-one (EBX) from the corresponding silyl protected reagent using TBAF is reported. EBX displayed exceptional acetylene transfer ability to stabilized enolates, even at –78 °C. The mild react ...

2010

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