A5063678551- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Asymmetric Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Synthesis and Catalytic Reactions
- Magnetism in coordination complexes
- Lanthanide and Transition Metal Complexes
- Crystallography and molecular interactions
- Advanced Synthetic Organic Chemistry
- Organoboron and organosilicon chemistry
- Multicomponent Synthesis of Heterocycles
- Medicinal plant effects and applications
- Advanced NMR Techniques and Applications
- Metal-Organic Frameworks: Synthesis and Applications
- Catalytic Alkyne Reactions
- Lichen and fungal ecology
- Catalytic C–H Functionalization Methods
- Cyclopropane Reaction Mechanisms
- Microbial Natural Products and Biosynthesis
- Synthesis and biological activity
- Vanadium and Halogenation Chemistry
- Carbohydrate Chemistry and Synthesis
- Analytical Chemistry and Chromatography
Université de Rennes
2015-2025
Centre National de la Recherche Scientifique
2014-2025
Institut des Sciences Chimiques de Rennes
2014-2024
STMicroelectronics (France)
2023
Université Rennes 2
2020
Indian Institute of Chemical Technology
2017
Institut de Chimie des Substances Naturelles
2010-2014
University of Florence
2007-2012
École Polytechnique Fédérale de Lausanne
2010
École Polytechnique
2010
Metal-free chiral phosphoric acids and calcium phosphates both catalyze highly enantio- diastereoselective electrophilic α-bromination of enecarbamates to provide an atom-economical synthesis enantioenriched vicinal haloamines. Either enantiomer can be formed in good yield with excellent diastereo- enantioselectivity simply by switching the catalyst from a acid its salt.
Abstract A field‐induced chiral Yb III Single‐Molecule Magnet (SMM) displayed an unprecedented near‐infrared circularly polarized luminescence (NIR‐CPL) in the solid‐state. The bridging bis(1,10‐phenantro[5,6b])tetrathiafulvalene triad ( L ) allowed efficient sensitization of NIR 2 F 5/2 → 7/2 emission while NIR‐CPL is associated to f ‐ transitions ion bearing β‐diketonate derived‐camphorate ancillary ligands.
Highly enantioselective direct amination of enamides catalyzed by chiral nonracemic calcium bis(phosphate) complex 3g afforded optically active 1,2-hydrazinoimines 4. Following a subsequent in situ hydrolysis or reduction, 2-hydrazinoketones 5 syn-1,2-disubstituted 1,2-diamines 6 were obtained high yields and excellent enantiomeric excess.
The classical Prins cyclization reaction has been one of the most studied reactions during last two decades and it found many applications in key steps natural product syntheses, especially for products containing pyran units related structures their core skeletons. nitrogen‐based version reaction, aza‐Prins cyclization, its own relevance organic synthesis owing to fact that gives direct access piperidines, which are even more widespread drugs. Even though potential scope is vast, despite...
Abstract A novel multicomponent synthesis of 5‐alkoxyoxazoles, based on a new reactivity profile α‐isocyanoacetates, is described. Thus, simply heating solution amine, aldehyde, and α‐(EWG‐phenyl)‐α‐isocyanoacetate or α‐(4‐pyridyl)‐α‐isocyanoacetate (EWG=electron‐withdrawing group) in toluene provided 5‐alkoxyoxazoles good to excellent yields. Reaction the with various α,β‐unsaturated acyl chlorides led formation epoxytetrahydropyrrolo[3,4‐b]pyridin‐5‐ones by domino N‐acylation/Diels–Alder...
The synergistic catalysis between a chiral phosphoric acid and CuCl allows the development of first enantioselective Prins cyclization.
A thorough phytochemical study of Stereocaulon evolutum was conducted, for the isolation structurally related atranorin derivatives. Indeed, pilot experiments suggested that (1), main metabolite this lichen, would interfere with lifecycle hepatitis C virus (HCV). Eight compounds, including one reported first time (2), were isolated and characterized. Two analogs (5, 6) also synthesized, to enlarge panel atranorin-related structures. Most these compounds active against HCV, a half-maximal...
The diastereoselective synthesis of 4-hydroxypiperidines bearing a tetrasubstituted carbon stereocenter at C4 by aza-Prins cyclization is presented. These motifs are relevant because they present in considerable number drugs.
Abstract A highly enantioselective, chiral, Lewis acid calcium–bis(phosphate) complex, Ca[ 3 a ] n , which catalyzes the electrophilic amination of enamides with azodicarboxylate derivatives 2 to provide versatile chiral 1,2‐hydrazinoimines 4 is disclosed. The reaction gives an easy entry optically active syn ‐1,2‐disubstituted 1,2‐diamines 6 in high yields excellent enantioselectivities, after one‐pot reduction intermediate . geometry and nature N‐substituent enamide affect dramatically...
An improvement in the catalytic enantioselective allylboration of isatins with 2-allyl-1,3,2-dioxaborolane presence chiral BINOL derivatives is reported, offering an efficient one-step access to enantioenriched N-unprotected 3-allyl-3-hydroxy-2-oxindoles. This process also effective for crotylboration reaction enantiomeric ratios (er) up 97:3, as well asymmetric synthesis homopropargylic alcohols via allenyl addition indoline-2,3-diones. Origins high enantioselectivity BINOL-catalyzed were...
Amination of enecarbamates with dibenzylazodicarboxylate and oxygenated nucleophiles in the presence a catalytic amount chiral phosphoric acid afforded optically active stable precursors α-hydrazinoimines, which were reduced or oxidized, respectively, to vicinal diamines α-amino excellent yield enantioselectivity.
Field-induced single-molecule magnet behavior and circularly polarized luminescence were observed in a series of ytterbium one-dimensional coordination polymers involving chiral BINOL-derived bisphosphate ligands.
Couple and cyclize: A coupling–cyclization strategy employing building blocks from the chiral pool was applied for generation of morpholine-containing scaffolds (see scheme). The modulation both reaction conditions stereochemistry allowed first degree skeletal diversity, followed by functional group pairing strategic appendages selected molecular to achieve more complex frameworks. Detailed facts importance specialist readers are published as "Supporting Information". Such documents...
A novel aza-Prins cyclization promoted by a synergistic combination between Lewis acid and Brønsted to efficiently afford piperidines is described. Contrary what has been previously reported in the literature, generality of reaction employing N-alkyl, N-aryl, nonprotected homoallylamines demonstrated. The highly diastereoselective depending on homoallylic amine used, N-PMP homoallyl leading preferentially trans diastereomer, free homoallylamine affording deprotected piperidine as single cis...
The nature of the aromatic system and number chiral centers BINOL derived bisphosphate ligands influence both chiroptical properties single-molecule magnet behavior a series dysprosium-based chains.
Abstract Piperidine derivatives are highly abundant in natural products and pharmaceutically relevant compounds. Aza‐Prins cyclization has emerged as a step‐ atom‐economical stereoselective method for the preparation of such azacycles. The possibility coupling aza‐Prins process with formation second cycle one‐pot manner is even more powerful makes object this review. Cascade/domino/tandem bis ‐cyclizations involving an process, rapid construction complex small molecules, discussed detail.
The enantiopure coordination polymer [Dy(hfac)<sub>3</sub>(<bold>(S/R)-L</bold>)]<sub>n</sub>(<bold>[(S/R)-1]n</bold>) involving a BINOL-derived bisphosphate ligand<bold>(S/R)-L</bold>is investigated both in solution and solid-state.
3-Allyl-3-hydroxyoxindoles are obtained with high ee in a metal-free catalytic process from isatins. This scaffold has been converted to the natural product chimonamidine.
Abstract The interest for lanthanide circularly polarized luminescence (CPL) has been quickly growing 10 years. However, very few of these studies have involved correlation between the dissymmetry factor ( g lum ) and chemical modifications in a series chiral ligands. Four polymeric compounds Eu(III) were prepared by using binaphtyl derivatives which size π system as well number stereogenic elements (i.e., moiety) are modulated. resulting {[Eu(hfac) 3 (( S )/( R )‐L x )]} n = 1 3) , 2 4)...
The application of sequential Ti-/Cu-catalysis in the model one-pot synthesis benzodiazepine(di)ones promoted by microwave irradiation demonstrates expediency dual catalysis coupling-cyclization methods useful for diversity-oriented synthesis.
The concise synthesis of a small library fluorinated piperidines from readily available dihydropyridinone derivatives has been described. effect the fluorination on different positions then evaluated by chemoinformatic tools. In particular, compounds' pKa's have calculated, revealing that fluorine atoms notably lowered their basicity, which is correlated to affinity for hERG channels resulting in cardiac toxicity. "lead-likeness" and three-dimensionality also assess ability as useful...
Over the past decade, chiral Lewis base-catalysed cycloadditions has brought about numerous methods for enantioselective synthesis of carbocycles and heterocycles. This short review covers some advances made in area absolute stereocontrol this higher order cycloaddition. Keywords: Cycloaddition, organocatalysis, asymmetric, base, phosphine catalysts, amine organic synthesis, asymmetric cycloaddition, Diels-Alder transformations, carbocycles, heterocycles, cyclopropanes, alkaloids, bioactive...
A systematic study on the phosphorylation of BINOL and other bis-phenols with chlorophosphates is described. An intriguing reactivity has been observed that attributable to hydroxyl group acidity leaving nucleofuge character within phosphorylating agent used. By playing these two parameters, new chiral monophosphotriesters, symmetrical homo-BINOL bisphosphates, unsymmetrical non-homo-BINOL derivatives incorporating a non-chiral side unit, were synthesized selectively in good yields.