Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jun-Hao Zhang, Hui Xu, Xiaodong Tang, Yanfeng Dang, Fa-Guang Zhang, Jun-An Ma
Summary: In this study, the efficient and stereoselective hydrogenation of congested tetra-substituted cyclic beta-enamido phosphonates/phosphine oxides was achieved using a commercially available Rh-Josiphos system. This method enables the synthesis of chiral beta-amino phosphorus compounds with two vicinal stereocenters. The protocol is applicable to various ring systems and different phosphonate/phosphine oxide groups, and it has been successfully applied to the preparation of amino-phosphine ligands. The DFT mechanistic explorations suggest that the C=C migratory insertion into the Rh-III-H bond is the rate- and stereo-determining step, and the origins of stereoselectivity are regulated by dispersion interactions and steric repulsions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shibaram Panda, Upasana Gayen, Prasanta Ghorai
Summary: This study describes the first organocatalytic, non-destructive desymmetrisation of 3-substituted cyclobutanone followed by intramolecular cyclisation. The use of cinchona-derived squaramide catalyst effectively enables the intramolecular Michael addition of cyclobutanone to enones, resulting in the formation of [6,5,4]-fused carbocyclic skeleton with good yields and excellent diastereo- and enantioselectivities. Moreover, this method provides an alternative pathway for the synthesis of enantioenriched high-value products like gamma-lactones and indan-2-ol derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Shu-Fang Wu, Guo-Ke Zhang, Xue Wang, Zhuo-Jing He, Yu-Chen Zhang, Feng Shi
Summary: The first organocatalytic diastereoselective (4 + 1) cycloaddition of o-hydroxyphenyl-substituted secondary phosphine oxides has been established, providing an efficient and diastereoselective method for constructing phosphorus-containing benzo five-membered heterocyclic skeletons with both P-stereocenter and C-stereocenter.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinping Yuan, Pankaj Jain, Jon C. Antilla
Summary: The catalytic asymmetric addition of beta,gamma-substituted allylboronates to aldehydes has been described, showing highly efficient and selective reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sumit B. Kamble, Ranjeet K. Bhore, Santosh G. Tilve
Summary: The method involves the construction of multifunctional ring fused octahydro 3-CN-2-pyridone decaline motifs using a single pot multicomponent, diastereoselective, organocatalytic domino approach. It has high diastereoselectivity, catalytic activity, high yields, cost-effectiveness, and a simple, mild, and operationally scalable process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Chao Che, Yi-Nan Lu, Chun-Jiang Wang
Summary: A novel strategy for catalytic asymmetric synthesis of enantioenriched 3-cis- and 3-trans-substituted prolines has been successfully developed via a unique cascade radical addition/cyclization enabled by synergistic photoredox/Bronsted acid catalysis and subsequent base-assisted epimerization. This method provides a de novo access to all four stereoisomers of 3-substituted prolines, which cannot be readily obtained using current established methods. The methodology can also be extended to the asymmetric synthesis of the full complement of stereoisomers of 3-substituted pipecolinic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Sheng Zuo, Yuan Tao, Zhigang Liu, Ke Zhang, Luyun Zhang, Yingtang Ning, Fen-Er Chen
Summary: This study successfully synthesized highly congested indanone-based spirolactones through copper-catalyzed decarboxylative propargylation, with the key role of DPEN-based ligands. The method tolerated a wide range of functional groups, yielding high diastereo- and enantioselectivities. Mechanistic observations indicated the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
Article
Chemistry, Multidisciplinary
Andrey D. Vinokurov, Taygib M. Iliyasov, Kirill A. Karpenko, Alexandra V. Evstigneeva, Alexandra P. Minaeva, Michail N. Elinson, Anatoly N. Vereshchagin
Summary: The Michael-Mannich-cyclization cascade reaction of four compounds leads to the stereoselective formation of halogenides with three stereogenic centers. Ammonium acetate acts as both a base and a nitrogen source.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Analytical
Shaocheng Liu, Man He, Beibei Chen, Xiao Yin, Qi Kang, Yan Xu, Bin Hu
Summary: In this study, a cascade amplification strategy combining strand displacement amplification (SDA) and multicomponent nucleic acid enzyme (MNAzyme) was proposed for detecting DNA MTase activity using AuNPs labeling inductively coupled plasma mass spectrometry (ICP-MS). The method demonstrated ultra-high sensitivity and was capable of highly sensitive detection in complex biological samples.
SENSORS AND ACTUATORS B-CHEMICAL
(2022)
Article
Chemistry, Multidisciplinary
Abdolali Alizadeh, Elham Sanjari, Reza Rezaiyehraad, Mohammad Reza Halvagar
Summary: This study presents a fast and efficient sequential three-component reaction for the synthesis of highly functionalized compounds. The reaction demonstrates short reaction time and simple product purification.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Lisa Moni, Luca Banfi, Andrea Basso, Alessia Mori, Federica Risso, Renata Riva, Chiara Lambruschini
Summary: The study reveals that different types of ferulic acid derivatives show varied behavior in the (E) to (Z) photoisomerization process at the photostationary state. Mixtures of (Z)/(E) ratios in the range from 7 : 93 to 72 : 28 are observed for esters and amides, while ketones exhibit limited photoisomerization. However, (Z) ketones can be obtained through the reaction of organometal compounds with a pre-isomerized (Z) Weinreb amide.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Federica Minuto, Chiara Lambruschini, Andrea Basso
Summary: The study successfully conducted a 3-component Staudinger reaction for the first time by mixing aldehydes, amines, and diazoketones in the dark and then turning on the light, achieving efficiency and selectivity comparable to traditional methods, providing a new approach for the synthesis of combinatorial libraries of compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Roberto Tinelli, Davide Ravelli, Andrea Basso, Serena C. Tarantino, Luca Capaldo
Summary: The catalyst-free [2 + 2] photocycloaddition between benzils and simple olefins was investigated to afford the expected oxetanes regio- and stereoselectively; the use of visible light was crucial for enhancing the selectivity of the reaction; lowering the reaction temperature consistently improved the selectivity of the transformation.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Jose Nunes da Silva Junior, Davila Zampieri, Antonio Jose Melo Leite Junior, Francisco Serra Oliveira Alexandre, Jean-Yves Winum, Andrea Basso, Andre Jalles Monteiro, Lucas Lima da Silva
Summary: A virtual Game-Based Tournament of Chemistry was developed as an alternative to traditional problem-solving classes, aimed at helping students review and understand organic acidity and basicity concepts. The tournament, based on a multilingual virtual board game, facilitated interactive and collaborative learning for students in an enjoyable activity. The findings showed that participating in the tournament resulted in better exam outcomes compared to traditional problem-solving classes.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Review
Chemistry, Multidisciplinary
Jose Nunes da Silva Junior, Jean-Yves Winum, Andrea Basso, Luca Gelati, Lisa Moni, Antonio Jose Melo Leite Junior, Jair Mafezoli, Davila Zampieri, Francisco Serra Oliveira Alexandre, Kimberly Benedetti Veja, Andre Jalles Monteiro
Summary: This paper presents a multi-lingual virtual card game that can be played on computers and smartphones. The game offers a fun and cooperative environment for students to play remotely or face-to-face with friends, while reviewing topics related to the structural theory of organic compounds. Evaluation from Brazilian and Italian undergraduate students showed positive feedback, and learning assessments indicate that the game promotes equivalent learning compared to traditional problem-solving classes.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Review
Chemistry, Multidisciplinary
Tommaso Francesco Piccinno, Andrea Basso, Fabrizio Bracco
Summary: A comparative study was conducted on the performance and perception of two groups of students involved in a peer review activity for writing chemical laboratory reports. The first group had mandatory participation, while the second group participated voluntarily. The study aimed to determine if the overall activity was more effective when students participated voluntarily. The results suggest that the use of peer evaluation in chemistry is influenced by the nature of the activity (voluntary or mandatory), and student perception is strongly influenced by whether the activity is obligatory or optional. Thus, voluntary participation could have a more profound and long-lasting beneficial effect on learning.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Chemistry, Multidisciplinary
Pietro Capurro, Valentina Ricciardiello, Paola Lova, Chiara Lambruschini, Stefano Protti, Andrea Basso
Summary: Amphiphilic aryl radicals generated from arylazo sulfones under visible light irradiation have been utilized in a solventylation strategy via hydrogen atom transfer. This protocol successfully achieves versatile functionalization of various olefins using carbon-centered radicals derived from acetone, acetonitrile, chloroform, methylene chloride, nitromethane, methyl acetate, and methyl formate under metal- and photocatalyst-free conditions.
Article
Chemistry, Applied
Lisa Moni, Franziska Merkt-Tasch, Bernhard Mayer, Sergio Mulone, Thomas J. J. Mueller, Renata Riva
Summary: A new library of uncommon furo[2,3-c]isoquinoline scaffold has been synthesized using Ugi multicomponent reaction and complex one-pot Pd-mediated double cyclization. This approach has successfully introduced substituents with electron donor properties directly linked to the scaffold in positions 1 and/or 8. The influence of an aromatic ring as a spacer and the substitution of the phenyl substituent in position 1 with a thiophene on the photophysical properties has been investigated, and a significant switch to green emitters has been observed for an amino donor substituent.
Article
Chemistry, Multidisciplinary
Carlo Chiorri, Pietro Capurro, Chiara Lambruschini, Lisa Moni, Walter Sgroi, Andrea Basso
Summary: The basics of organic chemistry nomenclature were introduced in a nonformal laboratory setting to both secondary school students and lay people. The laboratory consisted of three distinct but interconnected activities aimed at explaining the importance of associating a name to a molecular structure and how this knowledge can be relevant in everyday life. The overall goal was to generate interest in chemistry topics through fun and engaging activities.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Chemistry, Multidisciplinary
Pietro Marchi, Wei Wang, Cristian Puig, Ander Martin, Tullio Crovetto, Jalel Labidi, Renata Riva, Dario Cavallo, Lisa Moni
Summary: An efficient and smart synthesis of bis-alpha-ketoamides using biobased aldehydes, acetic acid, and bis-isocyanides has been presented. The synthesized compounds were evaluated for their effect on the crystallization behavior of PLLA. Only a few compounds showed significant enhancement in PLLA nucleation, suggesting the potential of the proposed combinatorial synthetic approach for the discovery of new efficient biobased polymer additives.
Article
Chemistry, Multidisciplinary
Samantha Caputo, Alessandro Kovtun, Francesco Bruno, Enrico Ravera, Chiara Lambruschini, Manuela Melucci, Lisa Moni
Summary: The carbocatalyzed synthesis of 2,3-disubstituted quinolines was achieved using a three-component reaction, followed by oxidation, with graphene oxide as a catalyst. The method exhibited simple reaction conditions, good functional group tolerance, and scalability.
Article
Chemistry, Multidisciplinary
Luca Banfi, Andrea Basso, Chiara Lambruschini, Lisa Moni, Renata Riva
Summary: This perspective celebrates the 100th anniversary of the discovery of the Passerini three component reaction, highlighting its importance and application in organic synthesis. The focus of this review is on the various ways to expand the utility of the Passerini reaction.
Article
Education, Scientific Disciplines
Jose Nunes da Silva Junior, Antonio Jose Melo Leite, Jean-Yves Winum, Andrea Basso, Ulisses Silva de Sousa, David Macedo do Nascimento, Samuel Moura Alves
Summary: This paper introduces a hybrid multilingual game for undergraduate students to review and reinforce concepts related to stereochemistry in a ludic, competitive, and collaborative environment. The students enjoyed playing the game and felt that it contributed to their learning.
EDUCATION FOR CHEMICAL ENGINEERS
(2021)
