- Asymmetric Synthesis and Catalysis
- Chemical Synthesis and Analysis
- Cyclopropane Reaction Mechanisms
- Asymmetric Hydrogenation and Catalysis
- Synthesis and Catalytic Reactions
- Synthetic Organic Chemistry Methods
- Coordination Chemistry and Organometallics
- Catalytic Cross-Coupling Reactions
- Organoboron and organosilicon chemistry
- Catalytic C–H Functionalization Methods
- Carbohydrate Chemistry and Synthesis
- RNA and protein synthesis mechanisms
- Click Chemistry and Applications
- Advanced Synthetic Organic Chemistry
- Chemical synthesis and alkaloids
- Synthesis and Biological Evaluation
- Chemical Reaction Mechanisms
- Catalytic Alkyne Reactions
- RNA modifications and cancer
- Synthesis and Properties of Aromatic Compounds
- Surface Chemistry and Catalysis
- Fluorine in Organic Chemistry
- Synthesis of β-Lactam Compounds
- Axial and Atropisomeric Chirality Synthesis
- Sulfur-Based Synthesis Techniques
Centre National de la Recherche Scientifique
2015-2024
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques
2015-2024
Université Paris Cité
2015-2024
Sorbonne Paris Cité
2012-2023
Molécules d'Intérêt Biologique
2000-2021
Vanderbilt University
2021
Texas A&M University
2021
Ningbo University
2021
Wenzhou University
2021
Lanzhou Institute of Chemical Physics
2021
Al together now: Aluminotriazoles are obtained in a fully chemo- and regioselective manner by copper-catalyzed cycloaddition of organic azides with mixed-aluminum acetylides (see scheme). The carbonaluminum bond, which is unaffected the first transformation, still able to react further different electrophiles. Detailed facts importance specialist readers published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted...
A simple choice: Ligands termed SimplePhos (L*), based on a chiral amino and flexible aryl groups the phosphorus atom, induce high enantioselectivity in copper-catalyzed conjugate addition allylic substitution of dialkyl zinc trialkyl aluminum reagents (see scheme; CuTC=copper thiophene carboxylate). Supporting information for this article is available WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z702186_s.pdf or from author. Please note: The publisher not responsible content...
This short review focuses on enantiopure planar chiral [2.2]paracyclophanes (pCps), a fascinating class of molecules that possess an unusual three-dimensional core and intriguing physicochemical properties. In the first part review, different synthetic strategies for preparing optically active pCps are described. Although classical resolution methods based synthesis separation diastereoisomeric products still dominate field, recent advances involving kinetic racemic compounds...
This perspective discusses the synthesis and (chir)optical properties of compact luminophores derived from [2.2]paracyclophane useful as building blocks for development CPL emitters.
The use of structurally similar chiral non-racemic azomethine ylides, nitrones and imines derived from 1,2-aminol alcohols in asymmetric dipolar cycloadditions is reviewed. This general survey underlines the great synthetic potential cycloadditions, especially a diversity-oriented approach enables direct comparison reactivity apparently closely related reactive systems.
Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by metalative cyclization. The carbon-aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This synthetic route provides novel entry heterocyclic organoaluminum reagents as well straightforward access 3,4,5-trisubstituted isoxazoles 1,3,4,5-tetrasubstituted pyrazoles.
We report herein a general, practical method based on asymmetric transfer hydrogenation (ATH) to control the planar chirality of range substituted [2.2]paracyclophanes (pCps). Our strategy enabled us perform both kinetic resolution (KR) racemic compounds and desymmetrization centrosymmetric meso derivatives synthetically useful scales. High selectivities (up 99% ee) good yields 48% for KRs 74% reactions) could be observed several poly-substituted paracyclophanes, including series...
The Ir-catalyzed asymmetric hydroboration of bicyclic hydrazines with ee and chemical yields up to 64% is reported. switch from rhodium iridium leads systematically opposite enantiomers in this desymmetrization reaction.
RNA targeting represents an original and promising approach to the discovery of new therapeutic tools against numerous diseases. The majority intracellular RNAs are noncoding that play key regulatory functions in many physiological processes. Among these RNAs, long (lncRNAs) constitute largest class transcripts have been shown important functional roles development disease In this work, we developed a set biochemical assays for efficient small-molecule lncRNA ligands selective their target,...
The reaction of cyclic and open-chain diastereomerically pure secondary organoboranes with diisopropylzinc allows the preparation dialkylzinc reagents good to excellent retention configuration as shown by deuterolysis CuI- Pd0-mediated reactions electrophiles. importance a high boron-zinc exchange rate obtain diastereoselectivity has been shown. Improvement configurational stability stereomeric purity zinc intermediates obtained using mono-isopinocampheylborane ((-)-IpcBH2) providing...
Alkynyldimethylaluminum reagents react with various aromatic and aliphatic acid chlorides in a fast efficient way. This reaction provides simple entry to numerous ynones, using readily available, inexpensive, nontoxic metalating agent, does not require any transition metal as catalyst.
[reaction: see text] Phosphoramidites based on BINOL readily react with trimethylaluminum in "noncoordinating" solvents, leading to the corresponding aminophosphine which is real ligand copper-catalyzed asymmetric transformations. This artifact explains experimental differences ring opening of meso bicyclic hydrazines using dialkylzinc or trialkylaluminum reagents as nucleophiles.
A small library of 1,5-triazole derivatives linking a diaminocyclopentadiol and aromatic ketones has been prepared screened using NMR fluorescent techniques against tRNALys3, the HIV reverse transcription primer. The comparison their binding properties to those 1,4-triazole isomers, previously discovered in fragment-based approach, outlines influence linker on affinity selectivity such an approach.
Spy swap: The interaction between an unlabeled RNA and ligands (red hexagon) can be monitored by 19F NMR spectroscopy using small fluorinated diamines (green star) as spy reporters (see scheme). This technique also enables the visualization of conformational capture a riboswitch its ligand. Detailed facts importance to specialist readers are published ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted authors. Please note:...
In this article, we report the preparation of a series [2.2]paracyclophane-fused coumarin systems through simple and general procedure involving transition-metal-catalyzed cyclization aryl alkynoates as key step. We also highlight influence [2.2]paracyclophane (pCp) motif its "phane" interactions on spectroscopic properties newly synthesized fluorophores, which emit in blue-green region visible spectrum (λem up to 560 nm) show extremely large Stokes shifts (up 230 nm). Finally, demonstrate...
We have developed a practical method to perform the reductive photocleavage of sulfonamides using thioureas as organophotocatalysts. This transformation, which tolerates variety substrates, occurs under mild reaction conditions in presence tetrabutylammonium borohydride reducing agent. Experimental and theoretical mechanistic investigations complete study, shedding light on nature active species involved photocatalytic process.
[reaction: see text] Terminal alumination of alkynes by DIBALH or trimethylaluminum can be performed in a simple manner the presence small amount triethylamine. This new Lewis-base-catalyzed process delivers mixed alkynyldialkylalanes great interest, without need an initial deprotonation step with lithium sodium derivatives followed transmetalation.
Catalytic asymmetric hydroboration can be successfully applied to meso bicyclic hydrazines. The resulting alcohols are of great synthetic interest and lead in a straightforward manner cyclopentanic diamino with good enantiomeric purity.
[reaction: see text] Alkynyldimethylaluminum reagents are easily available from terminal alkynes and trimethylaluminum via a triethylamine-catalyzed metalation. These compounds can react with various aromatic heterocyclic halides in the presence of palladium fast efficient way. This catalyzed cross-coupling reaction provides simple entry to numerous internal alkynes, using readily available, inexpensive, nontoxic metalating agent.
Eine einfache Wahl: Die Liganden L* mit chiralen Amino- und flexiblen Arylgruppen am Phosphoratom erhielten den Namen "SimplePhos". Sie bewirken eine hoch enantioselektive kupferkatalysierte konjugierte Addition allylische Substitution Dialkylzink- Trialkylaluminiumreagentien (siehe Schema; CuTC=Kupferthiophencarboxylat). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2007/z702186_s.pdf or from author. Please note: The publisher...
Aluminium "klickt" mit: Aluminotriazole resultieren aus einer vollständig chemo- und regioselektiven kupferkatalysierten Cycloaddition von organischen Aziden mit gemischten Aluminiumacetyliden. Die Kohlenstoff-Aluminium-Bindung steht anschließend für Reaktionen verschiedenen Elektrophilen bereit.
The supramolecular chiral recognition between rac-2a and several structured RNA leads to a distinct 19F NMR signal splitting. analysis of the diastereomeric pairs formed upon binding this racemic probe delivers topological footprint RNA. This phenomenon can be exploited investigate dynamic events involving structural equilibria, as demonstrated in melting experiment. work provides proof concept that small fluorinated moderate binders act external probes structures.
In this communication we report a new strategy toward ketopyranosides based on carbene-mediated activation of the anomeric C−H bond carbohydrates. By forming carbon−carbon after glycosylation step, approach enables preparation both α- and β-ketopyranosides from advanced precursors.