A5055178426- Asymmetric Synthesis and Catalysis
- Chemical Synthesis and Reactions
- Axial and Atropisomeric Chirality Synthesis
- Asymmetric Hydrogenation and Catalysis
- Catalytic Cross-Coupling Reactions
- Ionic liquids properties and applications
- Catalytic C–H Functionalization Methods
- Sulfur-Based Synthesis Techniques
- Coordination Chemistry and Organometallics
- Synthesis and Catalytic Reactions
- Molecular spectroscopy and chirality
- Chemical synthesis and alkaloids
- Chemistry and Chemical Engineering
- Oxidative Organic Chemistry Reactions
- Chemical Reaction Mechanisms
- Chemical Synthesis and Analysis
- Organoboron and organosilicon chemistry
- DNA and Nucleic Acid Chemistry
- Catalytic Alkyne Reactions
- Phenothiazines and Benzothiazines Synthesis and Activities
- Crystallization and Solubility Studies
- Organic Chemistry Cycloaddition Reactions
- Multicomponent Synthesis of Heterocycles
- Surfactants and Colloidal Systems
- Enzyme Catalysis and Immobilization
University of Turin
2020-2024
University of Naples Federico II
2024
National Interuniversity Consortium of Materials Science and Technology
2021-2022
Sapienza University of Rome
2015-2021
Torino e-district
2021
Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones afford non-C2 -symmetrical, axially chiral biaryl products, which are promising compounds ligands and organocatalysts. The rotational barrier required have two distinct atropisomers has been evaluated in products generated from by means DFT calculations HPLC. use reagents was necessary configurationally stable enantiomeric can be obtained good yield stereoselectivity. These also prepared...
Abstract Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones afford non‐ C 2 ‐symmetrical, axially chiral biaryl products, which are promising compounds ligands and organocatalysts. The rotational barrier required have two distinct atropisomers has been evaluated in products generated from by means DFT calculations HPLC. use reagents was necessary configurationally stable enantiomeric can be obtained good yield stereoselectivity. These also...
A straightforward and efficient protocol to promote the metalation/anionic Fries rearrangements of O-aryl carbamates, using for first time a lithium amide as metalating agent under aerobic/ambient-friendly reaction conditions, is reported. This approach enables sustainable preparation salicylamide derivatives with high levels chemoselectivity within ultrafast times, working at room temperature in presence air/moisture, environmentally responsible cyclopentyl methyl ether solvent....
<italic>Cinchona</italic> alkaloid derivatives featuring a guanidinium group in diverse positions efficiently catalyze the cleavage of RNA model compound 2-hydroxypropyl <italic>p</italic>-nitrophenyl phosphate (HPNP).
Abstract The catalytic application of chiral phosphoric acids (CPAs) from 2004 to date represents a true milestone for asymmetric organocatalysis. However, not only the free can be conveniently employed in numerous different synthetic methodologies, thus being strictly compliant concept “organocatalysis”, but also their metal salts. This review focuses on reactions which catalyst is alkali or alkaline‐earth phosphate.
Abstract Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed Fe 2 (SO 4 ) 3 n H O in glacial acetic acid exhibits good functional group compatibility, including that bulky substituents, can be extended one‐pot transformation aryltrimethylsilylacetylenes acetyl derivatives via a...
A chiral heterogeneous catalyst derivative of (-)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide is proven here to be efficient in a three-component asymmetric Passerini protocol, carried out deep eutectic solvent. Reaction conditions are mild and green, while enantioselectivity excellent. The was easily recovered reused with no decrease its catalytic activity.
Deep Eutectic Solvent (DES)-like mixtures, based on glycerol and different halide organic inorganic salts, are successfully exploited as new media in copper-free halodediazoniation of arenediazonium salts. The reactions carried out absence metal-based catalysts, at room temperature a short time. Pure target products obtained without the need for chromatographic separation. solvents fully characterized, computational study is presented aiming to understand reaction mechanism.
The global E factor (EG factor) has recently been introduced, in the context of asymmetric organocatalysis, as a new green chemistry metric to take into consideration synthesis catalyst overall economy synthetic process given chiral molecule optically pure form. Herein, its further usefulness comparing diverse catalytic systems, even different from organocatalysts, is shown by analysis four case studies.
Abstract The organocatalyzed addition of several malonates to 1,4‐benzoquinones affords benzofuranones bearing a quaternary stereocenter with good enantioselectivity. This reaction is an intramolecular desymmetrization since it proceeds through the formation arylated achiral malonate that cyclizes give product. rate quinone dramatically affects yield which was originally low. considerably increased, in some cases, from less than 20 % over 95 %, by adding portions rather at once, keeping...
An aggregation phenomenon involving <italic>Cinchona</italic> alkaloid derivatives deeply affects the performance of catalyst in an organocatalytic process – a mechanistic study.
Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Cu(I) catalysed Ullmann-type coupling. The synthetic protocols are mild and easy, produced either N-alkylanilines, aryl ethers, or thioethers fairly good yields (18 positive examples, average yield 66%). o-Benzenedisulfonimide was recovered at the end of reactions reused to prepare starting salts for further reactions. It is noteworthy that diazonium protocol first time.
A deep eutectic solvent (DES) based on glycerol and KF is successfully exploited as a medium in Ullmann homocoupling of arenediazonium salts. The reactions were carried out mild conditions target products obtained fairly good yields. computational study presented aiming to understand the reaction mechanism Raman spectroscopy employed an experimental tool support it.
Abstract A deep eutectic solvent (DES) based on glycerol and KF is successfully exploited as a medium in cross‐coupling reactions between arenediazonium o‐benzenedisulfonimides organolithium reagents (Muharashi‐Feringa coupling). The were carried out open air mild conditions. target products obtained fairly good yield (15 examples; average yield: 60 %). This is, the best of our knowledge, first example Muharashi‐Feringa coupling with diazonium salts. tentative hypothesis reaction mechanism...
Benzazetidines are highly strained and inherently unstable heterocycles. There only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate good yields (up 81%), it uses inexpensive materials does not require catalysts based on transition metals. The high ring strain energy of benzazetidine systems was estimated by density functional theory...
Abstract Time, energy, and cost saving; waste reduction; health safety preservation represent true milestones of green chemistry, as well some the most important aspects for industrial synthesis molecules having relevant technological applications. Herein, in light non‐conventional sustainable approaches towards polymethine dyes that appeared literature last decade, twelve principles chemistry serve a guideline critical overview such protocols. The E factor EcoScale score considered...
Abstract Chiral phosphoric acids (CPAs) and their salts are the privileged catalysts in a plethora of asymmetric transformations. All scaffolds efficient CPAs rely on C 2 ‐symmetry axial chirality, while only examples punctually chiral TADDOL derivatives. Herein, we present design synthesis ‐symmetric cycloglycerophosphates (cGPAs) application throughout addition trimethylsilyl cyanide (TMSCN) to aldehydes ketones, obtain corresponding cyanohydrins yields between 77 99% ee 84.2 99.5% (27...
Abstract Solketal, the chiral acetonide of glycerol, has been employed as starting material in design a novel punctually phosphate sodium salt for catalytic applications organic and asymmetric synthesis. The racemate two enantiomers substrate are economic commercially available, straightforwardly prepared high yields from naturally occurring feedstocks. Therefore, remarkably, both final catalyst can be synthesized by simple procedures yield compliance with several principles green chemistry....
A chiral glycerol derivative, namely 3-amino-1,2-propanediol, was employed for as the hydrogen bond donor (HBD) in design of a new deep eutectic solvent (DES) with choline chloride acting acceptor (HBA). The novel mixture characterized and unambiguously classified DES. Furthermore, its synthetic usefulness demonstrated room-temperature n-butyllithium-addition under air to carbonyl compounds benzyl chloride. In some cases, pure products (100% conversion) were obtained by simple extractive...