Review
Chemistry, Applied
Nuno G. Alves, Americo J. S. Alves, Maria I. L. Soares, Teresa M. V. D. Pinho e Meloa
Summary: Spirocyclic molecules, especially the spiro-lactams subclass, are highly valued for their complex three-dimensional features and structural rigidity, making them extensively explored for their bioactivity and utility in various scientific fields such as drug design and organic synthesis. Efforts have been made towards developing new synthetic strategies for spirocyclic lactams due to their broad potential, with significant advancements reported since 2015 in the synthesis of spiro-beta-lactams and spiro-delta-lactams.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Wenyang Wang, Ying Wang, Xiaowei Zhao, Wenjiao Yuan, Lei Zhang, Xiangtai Meng
Summary: We developed a NaH-promoted domino reaction between an azadiene bearing an indene moiety and a Nazarov reagent, leading to the synthesis of various substituted spiro[4.5]decane derivatives with good yields and high diastereoselectivity via [4+2] cycloaddition. The reaction conditions are mild and exhibit broad substrate scope. Furthermore, gram-scale experiment and transformation of the product were successfully carried out. Finally, DFT calculations were performed to confirm the proposed reaction mechanism and analyze the observed diastereoselectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yifei Huang, Mengting Tan, Nengzhong Wang, Yufei Zhang, Hui Yao, Xiao Xiao, Nianyu Huang, Kun Zou
Summary: A novel phosphine-catalyzed [2 + 4] annulation reaction was developed for the highly regio- and diastereoselective synthesis of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters. This method involves the reaction of benzofuran-derived azadienes with acidic hydrogen-tethered allyl carbonates and provides moderate to excellent yields under mild reaction conditions. Furthermore, the strategy presented in this study is practical, scalable, and offers a pathway for the synthesis of the core structural motif of the fungistatic drug griseofulvin.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hai-Jun Leng, Qing-Zhu Li, Peng Xiang, Ting Qi, Qing-Song Dai, Zhi-Qiang Jia, Chuan Gou, Xiang Zhang, Jun-Long Li
Summary: A novel oxindole-based azaoxyallyl cation synthons were designed for [3+1] cyclization with sulfur ylides, leading to facile production of 3,3-spiro[beta-lactam]-oxindoles with up to 94% yield and perfect diastereoselectivity.
Article
Chemistry, Multidisciplinary
Kajal Mal, Suman Ray, Suvendu Maity, Khondekar Nurjamal, Prasanta Ghosh, Goutam Brahmachari, Chhanda Mukhopadhyay
Summary: A new ultrasound-assisted method has been developed for the direct access to spiropyrido[2,1-b][1,3]oxazino compounds, which are structurally interesting and pharmacologically significant, via a three-component reaction approach. This method offers simple experimental and workup procedures, excellent yields, good functional group tolerance, cleaner reaction profiles, and the use of green solvents as remarkable features. Moreover, the use of ultrasound in this methodology leads to reduced reaction times.
Article
Chemistry, Organic
Hongcai Zhao, Zhengbing Zhang, Wenhua Lu, Pan Han, Wei Wang, Linhai Jing
Summary: A range of structurally novel CF3-containing spiro-delta-lactam oxindoles were successfully synthesized via the Michael/N-hemiketalization cascade reaction, with moderate to good yields and excellent diastereoselectivities. This work represents the first systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Juan-Carlos Castillo, Brian Castro Agudelo, Jaime Galvez, Yannick Carissan, Jean Rodriguez, Yoann Coquerel
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yun-Long Wei, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Jan Voigt, Myriam Roy, Milos Baljozovic, Christian Wackerlin, Yoann Coquerel, Marc Gingras, Karl-Heinz Ernst
Summary: The chiral self-assembly of trispentahelicene propellers on a gold surface has been investigated, demonstrating mirror domains with varying enantiomeric ratios and structural transformations during thermally induced cyclodehydrogenation.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Organic
Manuel Barday, Pierre Bouillac, Yoann Coquerel, Muriel Amatore, Thierry Constantieux, Jean Rodriguez
Summary: The progress in enantioselective organocatalysis has enabled efficient and highly stereoselective syntheses of cyclobutane derivatives. These derivatives can now be regarded as versatile building blocks for constructing larger rings through annulation reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Brian Castro Agudelo, Florian Rigoulet, Michel Giorgi, Babak Sayah, Jean Rodriguez, Yoann Coquerel
Summary: A class of cationic polycyclic aromatic compounds containing nitrogen atoms, known as azonia polycyclic aromatic compounds, were synthesized and their structural, optical, and conformational properties were studied using experimental and computational methods.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Albert Artigas, Denis Hagebaum-Reignier, Yannick Carissan, Yoann Coquerel
Summary: Visualization of electron delocalization and aromaticity in selected aryne compounds, including nonplanar examples, and their reactions was achieved using multidimensional isotropic magnetic shielding contour maps. The maps showed that aryne compounds are generally less aromatic than the corresponding arene compounds, with aromaticity peaking during the reaction when approaching the transition state.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Guillaume Dauvergne, Jean-Valere Naubron, Michel Giorgi, Xavier Bugaut, Jean Rodriguez, Yannick Carissan, Yoann Coquerel
Summary: The synthetic equivalents of enantiopure binaphthyl bis(aryne) atropisomers derived from BINOL have been generated in a solution for the first time. These atropisomers can be prepared enantiospecifically in high enantiomeric purity using various reactions, leading to potential applications in nanographene design.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Guillaume Dauvergne, Nicolas Vanthuyne, Michel Giorgi, Jean Rodriguez, Yannick Carissan, Yoann Coquerel
Summary: By combining theoretical calculations and experimental measurements, the kinetic constant of the cycloaddition reaction between a specially designed nonracemic aryne atropisomer and furan in solution was determined. The reaction half-life of this aryne atropisomer with 100 equivalents of furan as the trapping reagent was found to be <150 ns at temperatures above -20 degrees C.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Vincent S. Gutierrez, Axel Arnault, Veronique Ferreira, Albert Artigas, Denis Hagebaum-Reignier, Yannick Carissan, Yoann Coquerel, Marie-Aude Hiebel, Franck Suzenet
Summary: Pyrazine-fused 1,2,6,6a-tetrazapentalenes (PyTeAP) are zwitterionic tricyclic compounds with a unique pattern of four consecutive nitrogen atoms. Ten derivatives were successfully synthesized and the original scaffold of PyTeAP was confirmed through X-ray diffraction analysis. These compounds exhibited blue fluorescence in solution and theoretical investigations confirmed their aromaticity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Yoann Coquerel
Summary: The article briefly introduces the basics of arynes and their applications in synthetic organic chemistry, as well as defines the concept of atropisomerism. It discusses the differences between racemization and enantiomerization and presents the possibility of generating nonracemic aryne atropisomers. The synthetic applications of two structurally distinct aryne atropisomers and their potential for the synthesis of large PAH atropisomers with single handedness are also discussed.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Frederic Aribot, Amelie Merle, Pierre Dechambenoit, Harald Bock, Albert Artigas, Nicolas Vanthuyne, Yannick Carissan, Denis Hagebaum-Reignier, Yoann Coquerel, Fabien Durola
Summary: A rigid propeller-shaped conjugated triple macrocycle has been synthesized, consisting of two stacked benzene rings and three linking [5]helicene moieties, using a glyoxylic Perkin approach. Electron delocalization analysis of this atypical aromatic molecule revealed global aromaticity, with a 78 pi-electron circuit along the edge of its triple loop, at the expense of the two 6 pi-electron circuits in the stacked benzene rings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Albert Artigas, Florian Rigoulet, Michel Giorgi, Denis Hagebaum-Reignier, Yannick Carissan, Yoann Coquerel
Summary: This paper presents the synthesis and analysis of a highly contorted and doubly negatively curved multihelicene compound, made up of three carbo[7]helicene units fused within a central six-membered ring. The compound was synthesized through a [2 + 2 + 2] cycloaddition reaction of 13,14-picyne using a superior Ni(0) catalyst. The evaluation of aromaticity in this triple carbo[7]helicene challenged the limitations of Clar's model of aromaticity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Florian Rigoulet, Albert Artigas, Nawal Ferdi, Michel Giorgi, Yoann Coquerel
Summary: This study demonstrates that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Anthony Martin, Diana Cheshmedzhieva, Valeria Palermo, Frederic Lieby-Muller, Gustavo P. Romanelli, Anouk Gaudel-Siri, Yoann Coquerel, Thierry Constantieux, Jean Rodriguez
Summary: The regioselectivity of the oxidative three-component reaction between beta-ketoesters, aromatic o-diamines and acrolein, promoted by molecular sieves, has been investigated. The role of molecular sieves as a heterogeneous catalyst and dehydrating agent has been modeled in the theoretical approach. The influence of the nature of the substituents of the aromatic ring on the reactivity of the aromatic diamine partner and its impact on the regioselectivity of the reaction could be rationalized.
COMPTES RENDUS CHIMIE
(2022)
Article
Chemistry, Multidisciplinary
Albert Artigas, Denis Hagebaum-Reignier, Yannick Carissan, Yoann Coquerel
Summary: The electron delocalization in contorted polycyclic aromatic hydrocarbon (PAH) molecules was studied using 3D isotropic magnetic shielding (IMS) contour maps. The visualization of preferred electron circuits allowed for understanding of the local and global aromaticity patterns in the molecules. The differences in delocalization patterns between different faces of the electron circuits and diastereomeric chiral PAHs were clearly observed.
