Search results for: Maurizio Benaglia

Items from 1 to 20 out of 88 results

article

Enantioselective Organophotocatalytic Telescoped Synthesis of a Chiral Privileged Active Pharmaceutical Ingredient

Fabian Herbrik, Miguel Sanz, Alessandra Puglisi, Sergio Rossi, more

Chemistry – A European Journal > 28 > 33 > n/a - n/a

The continuous flow, enantioselective, organophotoredox catalytic asymmetric alkylation of aldehydes was studied, by using a homemade, custom‐designed photoreactor for reactions under cryogenic conditions. Going from microfluidic conditions up to a 10 mL mesofluidic reactor, an increase of productivity by almost 18000 % compared to the batch reaction was demonstrated. Finally, for the first time,...

article

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

Bárbara C. Lemos, Eclair Venturini Filho, Rodolfo G. Fiorot, Fabrizio Medici, more

European Journal of Organic Chemistry > 2022 > 2 > n/a - n/a

The enantioselective Povarov reaction is one of the most powerful synthetic strategy to synthesize chiral, highly functionalized 1,2,3,4‐tetrahydroquinolines. The present Minireview aims to collect the most significant successful examples of highly efficient enantioselective catalytic protocols for this reaction, since 2014. A comprehensive discussion of different catalytic strategies employed in...

article

Front Cover: Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings (Eur. J. Org. Chem. 32/2021)

Fabrizio Medici, Simonetta Resta, Piero Presenti, Lucia Caruso, more

European Journal of Organic Chemistry > 2021 > 32 > 4519 - 4519

The Front Cover shows how, like in a modern factory, it is possible to use light to build complex molecules in a continuous process. By exploiting chiral oxazolidinones, an efficient protocol for the in‐flow synthesis of enantiomerically enriched functionalized cyclopentane rings has been developed. The stereoselective light‐driven cyclization of bis(enones) in a coil photoreactor affords enantio‐enriched...

article

Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Fabrizio Medici, Simonetta Resta, Piero Presenti, Lucia Caruso, more

European Journal of Organic Chemistry > 2021 > 32 > 4521 - 4524

Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal‐free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in‐flow synthesis of enantiomerically...

article

Celebrating Franco Cozzi's 70th Birthday

Maurizio Benaglia, Cesare Gennari

European Journal of Organic Chemistry > 2021 > 29 > 4216 - 4217

On the occasion of the 70th birthday of Franco Cozzi (Università degli Studi di Milano), a selection of articles by his friends, colleagues, and former students, who are among the leading researchers in the field of Organic Chemistry in Italy, Europe, and overseas, covering the entire spectrum of synthetic organic, bioorganic, physical‐organic chemistry and organic stereochemistry, is presented.

article

Front Cover Picture: Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances (Adv. Synth. Catal. 14/2021)

Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi

Advanced Synthesis & Catalysis > 363 > 14 > 3379 - 3379

The front cover picture, designed by Sara and Luca Meninno, illustrates poorly reactive carboxylic acids and their ester and amide derivatives transformed into pyrazoleamides super‐molecules with superpowers. Where carboxylic acids, esters and amides fail pyrazoleamides succeed, allowing the transition from a world with limited possibilities to a rich and futuristic world, meeting the increasing needs...

article

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi

Advanced Synthesis & Catalysis > 363 > 14 > 3380 - 3410

Pyrazoleamides are a class of compounds which have received significant attention in the last years in asymmetric catalysis as more reactive and practical surrogates of esters or amides. These readily available reagents have served in a variety of diastereo‐ and enantioselective metal‐ and organocatalytic transformations, spanning from simple carbon‐carbon or carbon‐heteroatom bond formation to cascade...

article

Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles

Margherita Pirola, Chiara Faverio, Manuel Orlandi, Maurizio Benaglia

Chemistry – A European Journal > 27 > 40 > 10247 - 10250

A metal‐free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β‐substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and...

article

Amide Bond Formation Strategies: Latest Advances on a Dateless Transformation

Elisabetta Massolo, Margherita Pirola, Maurizio Benaglia

European Journal of Organic Chemistry > 2020 > 30 > 4641 - 4651

The synthesis of amides remains one of the most important transformations and it is one of the more frequently performed reactions. In the pharmaceutical industry, the formation of the amide group is pivotal and among the more important transformations in the design of the synthetic plan. This review presents an overview of only very recent contributions, published in the last three years, to highlight...

article

A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

Davide Brenna, Margherita Pirola, Laura Raimondi, Anthony J. Burke, more

Bioorganic & Medicinal Chemistry > 2017 > 25 > 23 > 6242-6247

The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode,...

article

Solid Supported Chiral N‐Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal‐ and Hydrogen‐Free Reduction of Imines in Batch and in Flow Mode

Riccardo Porta, Maurizio Benaglia, Rita Annunziata, Alessandra Puglisi, more

Advanced Synthesis & Catalysis > 359 > 14 > 2375 - 2382

A new class of solid supported chiral imidazolidinone organocatalysts for the catalytic reduction of imines with trichlorosilane has been developed. Polystyrene proved to be a more effective support than silica in terms of both chemical and stereochemical efficiency. Even with a loading as low as 1 mol% the best performing supported catalyst showed a remarkable activity and stereocontrol ability,...

article

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D‐Printed Mesoreactors

Sergio Rossi, Riccardo Porta, Davide Brenna, Alessandra Puglisi, more

Angewandte Chemie International Edition > 56 > 15 > 4290 - 4294

3D‐printed flow reactors were designed, fabricated from different materials (PLA, HIPS, nylon), and used for a catalytic stereoselective Henry reaction. The use of readily prepared and tunable 3D‐printed reactors enabled the rapid screening of devices with different sizes, shapes, and channel dimensions, aimed at the identification of the best‐performing reactor setup. The optimized process afforded...

article

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D‐Printed Mesoreactors

Sergio Rossi, Riccardo Porta, Davide Brenna, Alessandra Puglisi, more

Angewandte Chemie > 129 > 15 > 4354 - 4358

article

Stereoselective Metal‐Free Reduction of Chiral Imines in Batch and Flow Mode: A Convenient Strategy for the Synthesis of Chiral Active Pharmaceutical Ingredients

Davide Brenna, Maurizio Benaglia, Riccardo Porta, Silvia Fernandes, more

European Journal of Organic Chemistry > 2017 > 1 > 39 - 44

The convenient, metal‐free reduction of imines that contain an inexpensive and removable chiral auxiliary allowed for the synthesis of the immediate precursors of chiral active pharmaceutical ingredients (APIs). This protocol was carried out under batch and flow conditions to give the correspoding products in high yields with almost complete stereocontrol. In the presence of trichlorosilane, an inexpensive...

article

Synthesis of an advanced precursor of Rivastigmine: Cinchona-derived quaternary ammonium salts as organocatalysts for stereoselective imine reductions

Andrea Genoni, Maurizio Benaglia, Emanuele Mattiolo, Sergio Rossi, more

Tetrahedron Letters > 2015 > 56 > 42 > 5752-5756

The enantioselective reduction of ketoimines has been successfully realized, using trichlorosilane as the stoichiometric reducing agent in the presence of catalytic amounts of a Lewis base, specifically a Cinchona derivative. For the first time, a novel class of derivatives was studied, featuring a picolinamide unit bound to the alkaloid scaffold, further functionalized as quaternary ammonium salt...

article

A Stereoselective Catalytic Nitroaldol Reaction as the Key Step in a Strategy for the Synthesis of the Renin Inhibitor Aliskiren

Sergio Rossi, Maurizio Benaglia, Riccardo Porta, Livius Cotarca, more

European Journal of Organic Chemistry > 2015 > 11 > 2531 - 2537

Aliskiren is the first‐in‐class orally active direct renin inhibitor. It was approved in 2007 for the treatment of hypertension. We have designed a new strategy for the convergent synthesis of aliskiren that involves a catalytic stereoselective nitroaldol reaction as the key step. A new enantiopure nitroalkane (synthon A¹), prepared in only three steps from a commercially available enantiopure 2‐(arylmethyl)‐3‐methyl...

article

Continuous-Flow Stereoselective Synthesis in Microreactors: Nucleophilic Additions to Nitrostyrenes Organocatalyzed by a Chiral Bifunctional Catalyst

Sergio Rossi, Maurizio Benaglia, Alessandra Puglisi, Christian C. Filippo, more

Journal of Flow Chemistry > 2015 > 5 > 1 > 17-21

Metal-free stereoselective additions of activated nucleophiles to ß-nitrostyrenes were investigated under continuous-flow conditions in microreactors, in the presence of a chiral bifunctional catalyst. Optimization of the experimental setup gave excellent enantioselectivities (up to 85% e.e.) and higher productivities if compared to the flask syntheses. The potential of this flow chemistry approach...

article

Enantioselective Organocatalytic Reduction of β‐Trifluoromethyl Nitroalkenes: An Efficient Strategy for the Synthesis of Chiral β‐Trifluoromethyl Amines

Elisabetta Massolo, Maurizio Benaglia, Manuel Orlandi, Sergio Rossi, more

Chemistry – A European Journal > 21 > 9 > 3589 - 3595

An efficient organocatalytic stereoselective reduction of β‐trifluoromethyl‐substituted nitroalkenes, mediated by 3,5‐dicarboxylic ester‐dihydropyridines (Hantzsch ester type), has been successfully developed. A multifunctional thiourea‐based (S)‐valine derivative was found to be the catalyst of choice, promoting the reaction in up to 97 % ee. The methodology has been applied to a wide variety of...

article

Synthesis of novel chiral bithiophenebased phosphine oxides as Lewis bases in organocatalytic stereoselective reactions

Sergio Rossi, Maurizio Benaglia, Roberto Cirilli, Tiziana Benincori

Asymmetric Catalysis > 2015 > 2 > 1

Novel enantiomerically pure tetramethylbithiophene diphosphine oxides (tetraMe-BITIOPO) featuring differently substituted aromatic rings at the phosphorous atoms were synthesized, fully characterized and isolated in enantiomerically pure form. The new Lewis bases were tested as organocatalysts in two different reactions involving trichlorosilyl compounds. The introduction of electron donating substituents...

article

Synthesis of highly decorated chiral 2-nitro-cyclohexane carboxylic esters through microwave-assisted organocatalyzed cascade reactions

Elisabetta Massolo, Maurizio Benaglia, Davide Parravicini, Davide Brenna, more

Tetrahedron Letters > 2014 > 55 > 49 > 6639-6642

Starting from (E)-β-substituted-β-nitroacrylates and α,β-unsaturated ketones, a stereoselective organocatalyzed one-pot methodology allowed to synthesize highly decorated chiral 2-nitro-cyclohexane carboxylic esters. The reaction is promoted by Cinchona alkaloid-derived primary amines in the presence of an acidic co-catalyst and affords two diastereoisomers, in good yields and high enantiomeric excess...

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INFONA - science communication portal

Search results for: Maurizio Benaglia

Enantioselective Organophotocatalytic Telescoped Synthesis of a Chiral Privileged Active Pharmaceutical Ingredient

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

Front Cover: Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings (Eur. J. Org. Chem. 32/2021)

Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Celebrating Franco Cozzi's 70th Birthday

Front Cover Picture: Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances (Adv. Synth. Catal. 14/2021)

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles

Amide Bond Formation Strategies: Latest Advances on a Dateless Transformation

A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

Solid Supported Chiral N‐Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal‐ and Hydrogen‐Free Reduction of Imines in Batch and in Flow Mode

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D‐Printed Mesoreactors

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D‐Printed Mesoreactors

Stereoselective Metal‐Free Reduction of Chiral Imines in Batch and Flow Mode: A Convenient Strategy for the Synthesis of Chiral Active Pharmaceutical Ingredients

Synthesis of an advanced precursor of Rivastigmine: Cinchona-derived quaternary ammonium salts as organocatalysts for stereoselective imine reductions

A Stereoselective Catalytic Nitroaldol Reaction as the Key Step in a Strategy for the Synthesis of the Renin Inhibitor Aliskiren

Continuous-Flow Stereoselective Synthesis in Microreactors: Nucleophilic Additions to Nitrostyrenes Organocatalyzed by a Chiral Bifunctional Catalyst

Enantioselective Organocatalytic Reduction of β‐Trifluoromethyl Nitroalkenes: An Efficient Strategy for the Synthesis of Chiral β‐Trifluoromethyl Amines

Synthesis of novel chiral bithiophenebased phosphine oxides as Lewis bases in organocatalytic stereoselective reactions

Synthesis of highly decorated chiral 2-nitro-cyclohexane carboxylic esters through microwave-assisted organocatalyzed cascade reactions

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