Review
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Xiaoyu Yang
Summary: Helicenes and helicene-like molecules with unique helical chirality have found wide applications in various research fields. However, the catalytic enantioselective synthesis of helicenes has been relatively underexplored. In the past two decades, significant progress has been made in this field, including methods enabled by both transition metal catalysis and organocatalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Gagik G. Melikyan, Elen Artashyan, Shannen Guarina, Nicole Babayans, Masis Parunyan, Vahe Darabidian, Anurag Mishra
Summary: A stereoselective method for synthesizing five-and six-membered, mono-and binuclear carbocyclic compounds was developed by intramolecular cyclization of Co2(CO)6-complexed propargyl radicals. The formation of necessary bis-propargyl cations A relied on a stabilizing metal cluster, and the transient radicals were guided by a bulky metal core and substituents at the acetylenic termini. The cyclization reactions produced 1,2-dialkynylcyclopentanes and 1,2-dialkynylcyclohexanes with high stereoselectivity (91-100% trans-), and the addition of a gamma-TMS group enhanced the stereoselectivity by directing the cobalt-alkyne cores into diaxial positions. This work is important for the development of estrogen mimics.
Article
Chemistry, Multidisciplinary
Adrien Quintard
Summary: Selective copper catalysis activation of ketoacids, particularly bio-sourced 1,3-acetonedicarboxylic acid, and condensation with aldehydes under mild conditions, can lead to rapid preparation of natural product fragments and significant progress in this field through multicatalytic combination with organocatalysis. Additionally, cascade incorporation of fluorine offers new synthetic analogues with improved properties for a wide range of applications.
Article
Chemistry, Applied
Marta Meazza, Ramon Rios
Summary: This study describes the first synthesis of 2-alkenylquinolines from 2-allylquinolines and alpha,beta-unsaturated aldehydes. The reaction exhibits high regioselectivity and enantioselectivity, with a broad tolerance of functionalities in both the enal aromatic ring and the quinoline.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Inna V. Tatarinova, Natal'ya A. Lobanova, Igor' A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: Pure (E)-alkenoyl dihydropyrans can be stereoselectively assembled using a synthetic method, and they can be further transformed into 5-hydroxy-1,6-diketones and acetyl-2-(E)-styryl-2,3-dihydroxycyclopentanes through ring opening reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wei Huang, Jiahui Bai, Yinlong Guo, Qinglei Chong, Fanke Meng
Summary: A catalytic enantioselective coupling of 1,1-disubstituted allenes and aldehydes is achieved through regiodivergent oxidative cyclization followed by stereoselective protonation or reductive elimination promoted by chiral phosphine-Co complexes. This unprecedented reaction pathway for Co catalysis allows for the catalytic enantioselective generation of metallacycles with divergent regioselectivity accurately controlled by chiral ligands, leading to a wide range of allylic alcohols and homoallylic alcohols in high yields and excellent regioselectivity, diastereoselectivity, and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Adrien Quintard
Summary: In the past decade, multi-catalysis has become a popular alternative to traditional methods, offering rapid, efficient, and environmentally friendly ways to synthesize complex organic molecules. The use of iron-based catalysts has emerged as a cost-effective solution, with the added benefit of diverse reactivity features that expand the chemist's toolbox. These advantages position iron-based multi-catalysis as a leading technology for the future.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Saikat Das, Qiupeng Hu, Azusa Kondoh, Masahiro Terada
Summary: Enantioselective protonation of diarylphosphine oxides with 2-vinyl azaheterocycle N-oxide derivatives was achieved using chiral bis(guanidino)iminophosphorane as the catalyst, where a chiral weak conjugate acid played a crucial role as the proton source. This method allows for a broadening of enantioselective reaction systems by utilizing less acidic pronucleophiles, and enables the synthesis of chiral metal complex ligands through reduction of phosphine oxide and N-oxide units.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Physical
Srimanta Manna
Summary: Copper-catalyzed enantioselective borylative cyclization is a powerful tool for generating boron-containing carbocycles and heterocycles through the difunctionalization of unsaturated hydrocarbons. This review focuses on the copper-catalyzed borofunctionalization and enantioselective cyclization of alkenes, allenes, and alkynes, as well as the current understanding of the underlying mechanisms.
Review
Chemistry, Multidisciplinary
Huai-Ri Sun, Atif Sharif, Jie Chen, Ling Zhou
Summary: Atropisomeric heterobiaryls have gained significant interest from chemists in recent years for their crucial role in natural products, chiral ligands, organocatalysts, and other research fields. Various optically active heterobiaryls based on indole, quinoline, isoquinoline, pyridine, pyrrole, azole, and benzofuran skeletons have been successfully synthesized through metal or organic catalytic cross-coupling, functionalization of prochiral or racemic heterobiaryls, and ring formation. This review summarizes the enantioselective synthesis of axially chiral heterobiaryls through strategies such as cycloaddition, cyclization, and chirality conversion, along with the discussion of the reaction mechanism and the corresponding applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Na Shao, Valerie Monnier, Laurence Charles, Jean Rodriguez, Cyril Bressy, Adrien Quintard
Summary: This study reports a multicatalytic strategy for the synthesis of a new type of scaffold containing a tetrasubstituted stereocenter embedded in fluorohydrin motifs. The method involves organocatalyzed fluorination and diastereoselective aldol reaction, resulting in the stereoselective synthesis of fluorinated 1,3-diols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Vojtech Docekal, Tereza Koberova, Jan Hrabovsky, Andrea Vopalenska, Robert Gyepes, Ivana Cisarova, Ramon Rios, Jan Vesely
Summary: A new asymmetric organocatalytic cascade reaction was reported for the synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs), with high isolated yields and enantiomeric excesses. The method showed synthetic versatility and was successfully applied to a series of additional transformations of the corresponding optically pure compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Martina Sotolova, Martin Kamlar, Marek Remes, Pierre-Yves Geant, Ivana Cisarova, Martin Sticha, Jan Vesely
Summary: An organocatalytic asymmetric domino Michael/alpha-alkylation reaction has been developed for the synthesis of 1,2,3-trisubstituted cyclopentane carbaldehydes. The reaction, catalyzed by chiral secondary amines, exhibits high diastereo- and enantioselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Diksha Gambhir, Sanjay Singh, Ravi P. Singh
Summary: The rational combination of two catalysts has been widely used in the synthesis of biologically and pharmacologically relevant chiral compounds. This review article focuses on the achievements in asymmetric catalysis and synthesis using enamine and iminium-based dual organocatalytic systems. The combination of enamine/iminium catalysis with other organocatalytic systems has paved the way for the construction of complex chiral compounds.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Andrea Vopalenska, Vojtech Docekal, Simona Petrzelova, Ivana Cisarova, Jan Vesely
Summary: The present study reports an asymmetric organocascade reaction that efficiently catalyzes the reaction between oxindole-derived alkenes and 3-bromo-1-nitropropane using a bifunctional catalyst. The reaction produces spirooxindole-fused cyclopentanes in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol is demonstrated through additional transformations of the resulting spirooxindole compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Filip Bihelovic, Bojan Vulovic, Radomir N. Saicic
ISRAEL JOURNAL OF CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Andrew P. Cinderella, Bojan Vulovic, Donald A. Watson
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Milos Trajkovic, Zorana Ferjancic, Radomir N. Saicic, Filip Bihelovic
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Bojan Vulovic, Milena Trmcic, Radomir Matovic, Radomir N. Saicic
Review
Chemistry, Organic
Zorana Ferjancic, Radomir N. Saicic
Summary: The combination of organocatalytic aldol reaction and reductive amination allows for rapid, stereoselective synthesis of N-heterocycles, which is of great significance for the synthesis of iminosugars and other polyhydroxylated alkaloids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Milos Trajkovic, Milos Pavlovic, Filip Bihelovic, Zorana Ferjancic, Radomir N. Saicic
Summary: A chiral pyrrolidine derivative with 3 contiguous stereocenters was synthesized in only 2 synthetic steps from achiral precursors using a tactical combination of proline catalyzed aldol reaction followed by intramolecular reductive amination. This product, available in both enantiomeric forms, was further utilized as a common intermediate in total syntheses of biologically active iminosugars.
NATURAL PRODUCT COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Zorana Ferjancic, Andrej Kukuruzar, Filip Bihelovic
Summary: An enantioselective total synthesis of the monoterpenoid indole alkaloid (+)-alstonlarsine A (1) has been achieved, which possesses a unique pentacyclic skeleton and rare biological activity. The key step involves an efficient domino sequence, consisting of enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels-Alder cycloaddition for the construction of a 9-azatricyclo[4.3.1.0(3,8)]decane core. This strategy offers a new general entry into other tricyclic frameworks with fused indole ring and 6-, 7-, or 8-membered rings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zorana B. Ferjancic, Filip J. Bihelovic
Summary: This article focuses on the total synthesis of (+)-Alstonlarsine A and a novel methodology for indole C2 functionalization, providing new insights for the synthesis of other indole alkaloids.
Editorial Material
Chemistry, Multidisciplinary
Ksenija D. Glusac, Radomir N. Saicic
Summary: Does pursuing scientific research with a clear technological outcome hinder our creativity? Does it limit the chances to explore and develop fundamental areas of science that might lead to unforeseen applications?
Article
Chemistry, Organic
Filip Djurkovic, Zorana Ferjancic, Filip Bihelovic
Summary: The synthetic route leading to the successful enantioselective total synthesis of (+)-alstonlarsine A, a monoterpenoid indole alkaloid, is discussed. The key step involved the assembly of a unique 9-azatricyclo[4.3.1.0(3,8)]decane core through an efficient domino sequence. The development of a new method for introducing the phosphonoacetate moiety into the indole C-2 position was also described, enabling the synthesis of analogues with different substituent patterns.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Radomir N. Saicic, Milena Trmcic
Summary: Efforts to synthesize the cyclohexane core of antibiotic abyssomicin C were hindered by difficulties in the cyclization reaction, leading to the need for developing a new strategy to address this type of transformation.
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Filip Bihelovic, Zorana Ferjancic, Zlatko Joncev
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Medicinal
Filip Bihelovic, Bojan Vulovic, Radomir N. Saicic
NATURAL PRODUCT COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
