Search results for "chiral [effective Lagrangian]"
showing 10 items of 186 documents
Iminium Catalysis (n → π*)
2016
Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines
2017
A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinol L4 as the chiral ligand and Me2Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral β-amino esters, preserving in all cases the optical purity.
Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
2016
A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral b-amino esters with good yields and excellent enantioselectivities is reported.Areadily available diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral b-…
Input of P, N-(phosphanyl, amino)-ferrocene hybrid derivatives in late transition metals catalysis
2018
International audience; Unequally functionalized ferrocenes give access to valuable hemilabile reactivity in catalytic reaction. We address the synthesis of hybrid (P, N)-ferrocenyl compounds for which recent catalytic breakthrough applications have been reported, transversely in late transition metals chemistry. Palladium, nickel, rhodium, iridium, and emerging iron and gold catalysis are illustrated from selected examples, which include CC bond formation from cross-coupling and polymerization, allylic substitution, cyanation, hydroformylation, CH arylation and silylation and hydrogenation reactions.
Multivariate optimization approach for chiral resolution of drugs using human serum albumin in affinity electrokinetic chromatography-partial filling…
2005
The enantiomeric resolution of chiral compounds using HSA by means of affinity EKC (AEKC)-partial filling technique is the result of a delicate balance between different experimental variables such as protein concentration, running pH (background electrophoretic buffer, protein and compound solutions) and protein solution plug length. In this paper multivariate optimization approaches for chiral separation of four basic drugs (alprenolol, oxprenolol, promethazine and propranolol) using HSA as chiral selector in AEKC-partial filling technique are studied. The experimental conditions to achieve maximum resolution are optimized using the Box-Behnken experimental design. Partial least squares a…
Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives
2022
γ-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in the design of modern pharmaceuticals. For example, β-substituted GABA derivatives are found in numerous neurological drugs, such as baclofen, phenibut, tolibut, pregabalin, phenylpiracetam, brivaracetam, and rolipram, to mention just a few. In this review, we critically discuss the literature data reported on the preparation of substituted GABA derivatives using the Michael addition reaction as a key synthetic transformation. Special attention is paid to asymmetric methods featuring synthetically useful stereochemical outcomes and operational simplicity. This research was funded by the National Na…
On-surface Synthesis of a Chiral Graphene Nanoribbon with Mixed Edge Structure.
2020
Abstract Chiral graphene nanoribbons represent an important class of graphene nanomaterials with varying combinations of armchair and zigzag edges conferring them unique structure‐dependent electronic properties. Here, we describe the on‐surface synthesis of an unprecedented cove‐edge chiral GNR with a benzo‐fused backbone on a Au(111) surface using 2,6‐dibromo‐1,5‐diphenylnaphthalene as precursor. The initial precursor self‐assembly and the formation of the chiral GNRs upon annealing are revealed, along with a relatively small electronic bandgap of approximately 1.6 eV, by scanning tunnelling microscopy and spectroscopy.
Tetrazola hemiamināls kā hirāla palīggrupa
2017
Tetrazola hemiamināls kā hirāla palīggrupa. Sējējs M., zinātniskais vadītājs Prof., Dr. chem. Sūna E., konsultēja MSc. chem., Kinēns A. Maģistra darbs uzrakstīts latviešu valodā, tā apjoms 58 lapaspuses. Darbs satur 56 attēlus, 5 tabulas. Maģistra darbs veltīts terazolu hemiaminālu hirālās palīggrupas iegūšanai un pielietojumam diastereoselektīvajā sintēzē. Izstrādātās hirālās palīggrupas efektivitāte demonstrēta, ar augstu diastereoselektivitāti veicot karbonskābju α-pozīcijas fluorēšanas un nitrozo-aldola reakcijas. Darba rezultātā izstrādāts tetrazola hemiamināla hirālās palīggrupas stereoindukcijas modelis. Demonstrēta hirālās palīggrupas šķelšana maigos reakcijas apstākļos. Tetrazola h…
Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[b]benzofurans Based on Products from Anodic Oxidation of 2,4-Dimethylphenol
2015
The anodic treatment of 2,4-dimethylphenol offers a powerful and direct method for the construction of a dehydrotetramer with four contiguous stereocentres on a multigram scale. The installation of propellanes on this scaffold using enantiomerically pure carbonyl compounds leads to a mixture of diastereomers. This mixture is easily separable using standard chromatography and gives rise to optically pure cyclopenta[b]benzofurans which are important scaffolds in a variety of natural products. The synthesis is easy to perform and allows a reliable access to chiral compounds with very high enantiomeric excess. It was possible to determine the absolute configuration of these compounds by compari…
Installation of Amine Moieties into a Polycyclic Anodic Product Derived from 2,4-Dimethylphenol
2011
When 2,4-dimethylphenol is anodically treated, a dehydrotetramer with four contiguous stereocentres is readily obtained on a multi-gram scale. The substitution of a 2,4-dimethyl-phenoxy fragment by several amines was demonstrated, and the best results were obtained with primary amines. Optically pure α-chiral aliphatic amines yield diastereomeric mixtures that can be separated in most cases. The basic amine causes a partial hemiketal-opening of the bisbenzofuran moiety leading to an equilibrium within an α,β-unsaturated cyclohexenone. This dynamic behaviour occurs on the time scale of NMR spectroscopy and is also found by X-ray analysis providing a consistent picture.