Publications de Jérôme Waser

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We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process ...

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 ...

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 ...

The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic and carbocyclic compounds were obtained under mild conditions using Brønsted acid ca ...

Raw NMR, IR and MS data for the article "Iron-catalyzed synthesis of α-azido α-amino esters via alkylazidation of alkenes" published in Org. Lett. The number of the folders either correspond to compounds numbers in the article or the name of the folder is ...

A photochemical [2+2] cycloaddition of alkynyl boronates and maleimides is reported. The developed protocol provided 35–70 % yield of maleimide-derived cyclobutenyl boronates and demonstrated wide compatibility with various functional groups. The synthetic ...

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

First synthesized in 1991, EthynylBenziodoXolones (EBXs) - cyclic hypervalent iodine reagents derived from 2-iodobenzoic acid - are now among the most versatile electrophilic alkynylation reagents. Due to their cyclic structure, these reagents exhibit enha ...

1,1′-Bicyclopropenyl is a constitutional isomer of benzene comprising two coupled cyclopropene units with the endocyclic double bonds in conjugation. Due to the intrinsic high strain energy, it remains a long-standing challenge to prepare 1,1′bicyclopropen ...

A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at th ...

(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 ...

We report the detailed background for the discovery and development of the synthesis of homopropargylic azides by the azidoalkynylation of alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in a 29% yield of the desi ...

The first Ficini reaction between ynamides and acrylates is reported herein. The reaction is catalyzed by B(C6F5)3 acting as a Lewis acid and is giving access to stable tri-substituted aminocyclobutenes in high yield. The resulting products can be hydrogen ...

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...

A convenient one-step synthesis of beta-aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocataly ...

The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C-H functionalization of saturated O-heterocycles, as well as the deconstru ...

We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, eas ...

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 ...

The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solve ...

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 ...

Jérôme Waser

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Azido-alkynylation of alkenes through radical-polar crossover

Indole Alkaloids Synthesis via a Selective Cyclization of Aminocyclopropanes

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

Catalytic Formal Homo-Nazarov Cyclization

Raw data for article "Iron-catalyzed synthesis of α-azido α-amino esters via the alkylazidation of alkenes"

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues

Forging 1,1′-Bicyclopropenyls by Synergistic Au/Ag Dual-Catalyzed Cyclopropenyl Cross-Coupling

N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

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

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

Ficini Reaction with Acrylates for the Stereoselective Synthesis of Aminocyclobutanes

Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles

Photochemical Functionalization of Heterocycles with EBX Reagents: C-H Alkynylation versus Deconstructive Ring Cleavage

Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Pd-Catalyzed Intramolecular Oxyalkynylation of Alkenes with Hypervalent Iodine

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