Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Summary: A stereospecific three-component domino reaction was revealed under catalyst-free conditions, leading to the synthesis of a wide range of benzothiophene-fused polycycles and eight-membered N-heterocycles. The control over product formation was achieved by regulating the stereoconfiguration of cyclohexane-1,2-diamines. The detailed mechanism and origin of the chemoselectivity were explored using density functional calculations, revealing the influence of intramolecular attractions and steric effects on the observed chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Davit Hayrapetyan, Valeriya Stepanova
Summary: In this study, spirocyclic pyrrolidones and piperidones were synthesized via [3+2]- and [3+3]-aza-annulation reactions starting from readily available alpha-ketolactones and alpha-ketolactams. The annulation reactions proceeded with good yields and excellent diastereoselectivity, creating one C-C and two C-N bonds, as well as three new stereocenters in a fast and efficient manner.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla
Summary: The participation of reactants in polarity inversion allows the continuation of productive domino processes in multicomponent reactions, leading to the discovery of novel reaction pathways and various polyheterocyclic scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Quoc Hoang Pham, Andrew J. Tague, Christopher Richardson, Michael G. Gardiner, Stephen G. Pyne, Christopher J. T. Hyland
Summary: A Pd-catalysed (3 + 2) cycloaddition reaction of bis(trifluoroethyl) 2-vinyl-cyclopropane-1,1-dicarboxylate (VCP) with cyclic sulfamidate imine-derived 1-azadienes (SDAs) has been developed, leading to highly functionalized spiroheterocycles with three contiguous stereocentres, including a tetrasubstituted carbon bearing an oxygen functionality. The geminal trifluoroethyl ester groups can be selectively manipulated to afford spirocycles with four contiguous stereocentres. Additionally, reduction of the imine moiety can introduce a fourth stereocentre and expose a 1,2-amino alcohol functionality.
Article
Chemistry, Multidisciplinary
Yair Cohen, Andre U. Augustin, Laura Levy, Peter G. Jones, Daniel B. Werz, Ilan Marek
Summary: The regio- and diastereoselective copper-catalyzed carbomagnesiation reaction of cyclopropenes provides an easy and efficient access to novel persubstituted cyclopropyl cores with complete regio- and diastereoselectivity, despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Niklas Rauscher, Line Noesborg, Christian Jandl, Thorsten Bach
Summary: In this study, the prezizane-type sesquiterpene agarozizanol B was synthesized through a photochemical cascade reaction, successfully achieving the key step of the synthesis with a specific strategy and obtaining the (+)-enantiomer that is identical to the natural product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yate Chen, Zhengtian Ding, Yiming Wang, Wenfeng Liu, Wangqing Kong
Summary: This study describes an unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies suggest that indanones are formed through cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Peter Langer
Summary: The reaction of 1,3-bis(silyloxy)-1,3-butadienes with acid chlorides yields a variety of carbonyl compounds and cyclic products, while methylation and cyclopropanation reactions do not provide the expected products and require stepwise protocols.
Review
Biochemistry & Molecular Biology
Alessandro Massi, Olga Bortolini, Daniele Ragno, Tatiana Bernardi, Gianni Sacchetti, Massimo Tacchini, Carmela De Risi
Article
Chemistry, Organic
Graziano Di Carmine, Daniele Ragno, Carmela De Risi, Olga Bortolini, Pier Paolo Giovannini, Giancarlo Fantin, Alessandro Massi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Inorganic & Nuclear
Luciano Canovese, Fabiano Visentin, Thomas Scattolin, Claudio Santo, Valerio Bertolasi
Article
Chemistry, Multidisciplinary
Daniele Ragno, Arianna Brandolese, Daniele Urbani, Graziano Di Carmine, Carmela De Risi, Olga Bortolini, Pier Paolo Giovannini, Alessandro Massi
REACTION CHEMISTRY & ENGINEERING
(2018)
Article
Plant Sciences
Massimo Tacchini, Ilaria Burlini, Tatiana Bernardi, Carmela De Risi, Alessandro Massi, Alessandra Guerrini, Gianni Sacchetti
Review
Chemistry, Organic
Carmela De Risi, Olga Bortolini, Graziano Di Carmine, Daniele Ragno, Alessandro Massi
SYNTHESIS-STUTTGART
(2019)
Article
Biochemistry & Molecular Biology
Tatiana Bernardi, Olga Bortolini, Alessandro Massi, Gianni Sacchetti, Massimo Tacchini, Carmela De Risi
Article
Chemistry, Applied
Apurba Bhunia, Valerio Bertolasi, Subal Chandra Manna
APPLIED ORGANOMETALLIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Arianna Brandolese, Daniele Ragno, Costanza Leonardi, Graziano Di Carmine, Olga Bortolini, Carmela De Risi, Alessandro Massi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Daniele Ragno, Costanza Leonardi, Graziano Di Carmine, Olga Bortolini, Arianna Brandolese, Carmela De Risi, Alessandro Massi
Summary: A new N-heterocyclic carbene (NHC)-catalyzed strategy was developed for the regioselective monoesterification of isosorbide (IS) at specific positions, using aldehydes as acylating agents under oxidative conditions. Experimental evidence suggests the role of stereoelectronic features in determining the acylation selectivity, and the strategy showed promising results in producing monoacyl-isosorbides with satisfactory regioselectivity levels. Additionally, the heterogeneous phase application of the exo-selective triazolium salt promoter in continuous-flow catalysis demonstrated comparable catalytic activity and regioselectivity to the homogeneous counterpart.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Daniele Ragno, Carmela De Risi, Alessandro Massi, Graziano Di Carmine, Sofia Toldo, Costanza Leonardi, Olga Bortolini
Summary: A novel NHC-promoted synthesis method for biologically active isosorbide imidates was described. The method allows the easy synthesis of different benzothiazole products by using accessible aldimines and oxidative conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Carmela De Risi, Arianna Brandolese, Graziano Di Carmine, Daniele Ragno, Alessandro Massi, Olga Bortolini
Summary: Oxidative N-heterocyclic carbene (NHC) catalysis enables oxidative and oxygenative transformations, producing various NHC-bound intermediates and facilitating non-umpolung processes by activating carbon atoms and heteroatoms. This review discusses the developments in the literature on oxidative NHC catalysis since 2014, with a specific focus on pivotal intermediates and their mechanistic involvement.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Carmela De Risi, Arianna Brandolese, Graziano Di Carmine, Daniele Ragno, Alessandro Massi, Olga Bortolini
Summary: Oxidative N-heterocyclic carbene (NHC) catalysis has the potential to achieve oxidative and oxygenative transformations, generating various NHC-bound intermediates and enabling non-umpolung processes through the activation of carbon atoms and heteroatoms. This review aims to discuss the recent developments in the field of oxidative NHC catalysis since 2014, with a focus on pivotal intermediates and their mechanistic involvement. More details can be found in the review article by C. De Risi and co-workers.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Marco Bottin, Graziano Di Carmine, Olga Bortolini, Carmela De Risi, Monica Bertoldo, Tommaso R. I. Cataldi, Cosima D. Calvano, Alessandro Massi, Daniele Ragno
Summary: This article presents an alternative synthetic route to macrocyclic oligoesters (MCOs) using N-heterocyclic carbene (NHC) catalysis under highly diluted oxidative conditions. The method allows for the straightforward access to MCOs using commercial dialdehydes, without the use of toxic diacyl chlorides commonly employed in traditional processes. The method is metal-free, takes place in a green solvent, and uses a recyclable quinone oxidant.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Carmela De Risi, Olga Bortolini, Arianna Brandolese, Graziano Di Carmine, Daniele Ragno, Alessandro Massi
REACTION CHEMISTRY & ENGINEERING
(2020)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
