Article
Chemistry, Applied
Takaaki Aijima, Shinsuke Komagawa, Shuji Akai, Yoshinari Sawama
Summary: In this study, it was found that Siloxy-4-(benzyloxy)methyl-1,4-epoxy-1,4-dihydronaphthalenes can undergo automatic site-selective ring opening and subsequent annulation with olefins to form multi-fused heterocycles. The study also revealed the solvent-dependent regioselectivity in certain reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Marcos Escolano, Daniel Gavina, Santiago Diaz-Oltra, Maria Sanchez-Rosello, Carlos del Pozo
Summary: The enantioselective synthesis of fluorinated indolizidinone derivatives is achieved through an intramolecular aza-Michael reaction, followed by dimethyltitanocene methylenation and ring closing metathesis (RCM). The final products contain a fluorine-containing tetrasubstituted double bond generated by the RCM reaction, demonstrating high challenge. The synthetic sequence exhibits excellent enantioselectivities with acceptable overall yields.
Article
Chemistry, Multidisciplinary
Dennis Rottschafer, Timo Glodde, Beate Neumann, Hans-Georg Stammler, Diego M. Andrada, Rajendra S. Ghadwal
Summary: The newly synthesized compound 5 is a red crystalline solid with an 8π electron C4As2 ring, exhibiting antiaromaticity. It can undergo oxidation reaction to form compound 6 with a 6π electron aromatic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Gilles Lemiere, Alexandre Millanvois, Cyril Ollivier, Louis Fensterbank
Summary: This account describes less than ten years of acquaintance with hypercoordinated silicon derivatives in our lab, highlighting Martin's spirosilane derivatives as new opportunities for ligands and agents in small molecule activation, and bis-catecholato silicates as exquisite radical precursors in photoredox conditions for broad synthetic applications.
Article
Chemistry, Organic
Freya M. M. Harvey, Alexandra H. H. Heidecker, Christian Merten, Thorsten Bach
Summary: Allenes with different substituents at their terminal carbon atom exhibit axial chirality and can be obtained in enantiopure form through a photochemical deracemization protocol. This study investigates the conditions under which allenoic acid derivatives undergo a Diels-Alder reaction with 1,3-cyclopentadienes and the resulting products. Cyclic derivatives (lactams, lactones) exhibited an exo-selective reaction catalyzed by the Lewis acid Eu(fod)(3), while acyclic derivatives mainly produced endo-products (with EtAlCl2 as the preferred Lewis acid). The exocyclic double bond exhibited excellent diastereoselectivity and achieved near-perfect chirality transfer. The method was successfully applied to the synthesis of sesquiterpenes beta-santalol (1) and 10(E)-beta-santalic acid (13).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Applied
Xiangyu Li, Dennis G. Hall
Summary: This review highlights the significance of alpha-aminoalkylboronic acids and beta-aminoalkylboronates in medicinal chemistry, and explores their potential as bioisosteres of amino acids. It also discusses the versatile synthetic intermediates of beta-aminoalkylboronates and their role as catalysts in organic reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jana Sendra, Efraim Reyes, Liher Prieto, Elena Fernandez, Jose L. Vicario
Summary: Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid, providing high yields and excellent stereocontrol in the formation of complex adducts. These adducts can be converted into versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N-N cleavage.
Article
Chemistry, Physical
Yao Luo, Qi Wei, Liangkun Yang, Yuqiao Zhou, Weidi Cao, Zhishan Su, Xiaohua Liu, Xiaoming Feng
Summary: The synthesis of chiral ketones has been a significant focus in chemistry research. In this study, researchers successfully achieved a highly selective radical hydroacylation reaction for α-substituted α,β-unsaturated carbonyl compounds using anthraquinone photocatalyst and chiral N,N'-dioxide/metal complexes. This method provides a mild and robust approach to access a wide range of chiral ketones with α-tertiary stereocenters.
Article
Chemistry, Physical
Jacob Werth, Matthew S. Sigman
Summary: The study utilizes multivariate linear regression analysis to investigate different categories of BOX catalyzed reactions, developing predictive models for various asymmetric catalytic reactions including Cu, Ni, Fe, Mg, and Pd complexes, and reveals the structural requirements necessary for high selectivity through analysis of diverse organometallic intermediates.
Article
Chemistry, Organic
Jiwon Jang, Youngjin Bae, Seunghoon Shin
Summary: The gold-catalyzed formation of allyl sulfonium intermediates enables an exceptional level of control for the synthesis of skipped 1,4-dienes. However, the use of cinnamyl thioether derivatives in this reaction has been unsuccessful due to the dissociation of the cinnamyl cation. By tuning the bisphosphine ligands, cinnamyl thioethers can be successfully engaged in the rearrangement to yield the desired 1,4-dienes in good yields and with high enantioselectivity. The resulting products can be further transformed into optically active molecules.
Article
Parasitology
Elora Valderas-Garcia, Cecile Haberli, Maria Alvarez-Bardon, Nerea Escala, Veronica Castilla-Gomez de Aguero, Jennifer de la Vega, Esther del Olmo, Rafael Balana-Fouce, Jennifer Keiser, Maria Martinez-Valladares
Summary: This study evaluated the potential anthelmintic activity of three series of compounds against two gastrointestinal nematodes. Two compounds showed activity against the adult stage of the parasites, suggesting they could be a starting point for further compound synthesis.
PARASITES & VECTORS
(2022)
Article
Chemistry, Applied
Nemrud Demirel, Jie Qin, Sergei I. Ivlev, Klaus Harms, Eric Meggers
Summary: A method for the diastereoselective and enantioselective construction of 2,3-disubstituted 1,4-dicarbonyl compounds is reported in this study, utilizing Nishiyama's RuPhebox complex as a chiral Lewis acid catalyst to achieve stereocontrolled reaction of 2-acyl imidazoles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Hacer Can Uskup, Tulay Yildiz, Hulya C. Onar, Belma Hasdemir
Summary: In this study, new derivatives (substituted arenoxy) of 1,4-diketone compounds were synthesized using a new version of the Stetter reaction method. The reaction was catalyzed by 3benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, with triethylamine as the basic medium and dimethyl sulfoxide as the solvent. Some novel arenoxy-substituted 1,4-diketones were obtained with good yields at room temperature within 24 hours through an intermolecular Stetter reaction.
Article
Chemistry, Organic
Jannis Nonnhoff, Hans-Georg Stammler, Harald Groeger
Summary: This work describes an enantioselective biocatalytic synthesis of chiral thiomorpholines using imine reductases as catalysts. Prochiral and chiral 3,6-dihydro-2H-1,4-thiazines were synthesized and subsequently reduced using imine reductases, resulting in chiral thiomorpholines with high enantioselectivities. Additionally, a sequential one-pot process combining both reaction steps was achieved as a proof of concept.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Parasitology
Elora Valderas-Garcia, Jennifer de la Vega, Maria Alvarez Bardon, Veronica Castilla Gomez de Aguero, Ricardo Escarcena, Jose Luis Lopez-Perez, Francisco A. Rojo-Vazquez, Arturo San Feliciano, Esther del Olmo, Rafael Balana-Fouce, Maria Martinez-Valladares
Summary: The study evaluated the efficacy of various derivatives against Gastrointestinal nematodes, with diamine 30 showing the best results in preventing egg hatching and diamine 34 showing the highest efficacy in inhibiting larval migration.
VETERINARY PARASITOLOGY
(2021)
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)
