Tetrahedron Letters, Год журнала: 2022, Номер 112, С. 154221 - 154221
Опубликована: Окт. 31, 2022
Язык: Английский
Chinese Chemical Letters, Год журнала: 2023, Номер 34(10), С. 108559 - 108559
Опубликована: Май 13, 2023
Язык: Английский
Процитировано
13
JACS Au, Год журнала: 2023, Номер 3(6), С. 1742 - 1754
Опубликована: Май 26, 2023
A new generation of chiral gold(I) catalysts based on variations complexes with JohnPhos-type ligands a remote C2-symmetric 2,5-diarylpyrrolidine have been synthesized different substitutions at the top and bottom aryl rings: from replacing phosphine by N-heterocyclic carbene (NHC) to increasing steric hindrance bis- or tris-biphenylphosphine scaffolds, directly attaching C2-chiral pyrrolidine in ortho-position dialkylphenyl phosphine. The tested intramolecular [4+2] cycloaddition arylalkynes alkenes atroposelective synthesis 2-arylindoles. Interestingly, simpler led formation opposite enantiomers. binding pockets analyzed DFT calculations. As revealed non-covalent interaction plots, attractive interactions between substrates direct specific enantioselective folding. Furthermore, we introduced open-source tool NEST, specifically designed account for effects cylindrical-shaped complexes, which allows predicting experimental enantioselectivities our systems.
Язык: Английский
Процитировано
12
Israel Journal of Chemistry, Год журнала: 2022, Номер 63(9)
Опубликована: Авг. 29, 2022
Abstract Gold catalysis has emerged as an efficient tool for the selective functionalisation of C−C multiple bonds. Despite significant progress in this field, potential asymmetric gold not been fully explored to date. A historical retrospect on area reveals that enantioselective is based three pillars: Au(I) catalysis, Au(III) and Au(I)/Au(III) redox catalysis. Irrespective mode being operative, design new ligands crucial development gold‐catalysed organic transformations. This minireview summarizes made ligand focusing which were specially designed
Язык: Английский
Процитировано
17
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)
Опубликована: Окт. 24, 2023
Two different classes of stereoselective cyclizations have been developed using a chiral auxiliary approach with commercially available [JohnPhosAu(MeCN)SbF6 ] as catalyst. First, cascade cyclization 1,5-enynes was achieved the Oppolzer camphorsultam auxiliary. In this case, one-pot cyclization-hydrolysis sequence to directly afford enantioenriched spirocyclic ketones. Then, alkoxycyclization 1,6-enynes mediated by an Evans-type oxazolidinone. A reduction-hydrolysis selected remove give β-tetralones. DFT studies confirmed that steric clash between and alkene accounts for experimentally observed diastereoselective through Si face.
Язык: Английский
Процитировано
11
Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(28)
Опубликована: Май 4, 2022
The confinement of a catalytic site is an efficient strategy to control reaction and modulate its selectivity. In the present work, new class structurally simple easily accessible bulky tri-(ortho-biaryl)phosphine ligands were accessed, their gold(I) complexes synthesized. Their X-ray diffraction analysis comparative evaluation VBur % G steric parameters against series gold commonly employed in catalysis demonstrated confined nature. Despite notable congestion, these exhibited remarkable activities unusual selectivities, both nature level, that make them unique field synthetic homogeneous catalysis.
Язык: Английский
Процитировано
16
European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(38)
Опубликована: Июнь 23, 2022
H-bonded counterion-directed catalysis (HCDC) is a strategy wherein chiral anion that hydrogen-bonded to the achiral ligand of metal complex responsible for enantioinduction. In this article we present application Au(I)-catalyzed enantioselective tandem cycloisomerization-addition reaction 2-alkynyl enones. Following addition C-, N- or O-centered nucleophiles, bicyclic furans were obtained in moderate excellent yield and enantioselectivity (28 examples, 59-96 % yield, 62 : 38 95 5 er). The optimal catalytic system, comprising phosphinosquaramide Au(I) chloride BINOL-derived phosphoramidate Ag(I) salt, was selected combinatorial fashion from larger library with help high-throughput screening. An switch ca. 120 Δee% observed upon component salt.
Язык: Английский
Процитировано
15
Molecules, Год журнала: 2024, Номер 29(24), С. 5854 - 5854
Опубликована: Дек. 11, 2024
The advancement of synthetic host–guest chemistry has played a pivotal role in exploring and quantifying weak non-covalent interactions, unraveling the intricacies molecular recognition both chemical biological systems. Macrocycles, particularly calix[4]resorcinarene-based cavitands, have demonstrated significant utility receptor design, facilitating creation intricately organized architectures. Within realm macrocycles, these cavitands stand out as privileged scaffolds owing to their adaptability, excellent topological structures, unique properties. So far, extensive investigations been conducted on various applications cavitands. In this review, we will elaborate diverse functions, including catalysis, separation purification, polymeric materials, sensing, battery well drug delivery. This review aims provide holistic understanding multifaceted roles across applications, shedding light contributions advancing field supramolecular chemistry.
Язык: Английский
Процитировано
3
ACS Catalysis, Год журнала: 2025, Номер 15(3), С. 2342 - 2350
Опубликована: Янв. 24, 2025
The concise modular synthesis of a family monodentate 1,2-disubstituted ferrocene ligands containing diaryl phosphine and 2-aryl indole is described. Their gold(I) complexes were applied to the enantioselective gold(I)-catalyzed formal [4 + 2] cycloaddition 1,6-arylenynes, enyne cyclization/nucleophile addition N-tethered 1,6-enynes, methoxycyclization 1,6-arylenynes with high levels enantioselectivity in all cases. Crystallographic computational studies highlighted relevant role noncovalent interactions within ligand scaffold between substrate modes enantioinduction cyclization unsaturated substrates. Our recently developed open-source tool NEST was analyze chiral pockets catalysts, which combination RDKit allowed us understand these reactions, paving way for predictive-based approach toward rational development Au(I) catalysis.
Язык: Английский
Процитировано
0
Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown
Опубликована: Апрель 28, 2025
Abstract Gold catalysis has witnessed remarkable advances over the past decade, with numerous insightful reviews chronicling this progress. However, a comprehensive review addressing developments in field during post‐pandemic COVID era remains notably absent. This aims to bridge that gap by providing an in‐depth analysis of recent studies, shedding light on unique properties gold complexes, particularly intriguing aurophilic interactions distinguish chemistry. The systematically explores latest achievements both mono‐ and dinuclear gold‐catalyzed reactions, focus their applications diverse fields, including redox coupling, asymmetric catalysis, photo‐, electrocatalysis. A special emphasis is placed comparative performance catalysts, latter often exhibiting enhanced catalytic efficiency selectivity certain reactions. By integrating mechanistic insights DFT perspectives representative experimental studies from years, highlights significance synthetic chemistry, identifies emerging trends outlines future directions for field.
Язык: Английский
Процитировано
0
Coordination Chemistry Reviews, Год журнала: 2021, Номер 445, С. 214066 - 214066
Опубликована: Июнь 22, 2021
Язык: Английский
Процитировано
19