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Article
Simple synthesis of erythro-2,3,6-trimethylhepta-4,6-dien-1-ol acetate, a lasiol precursor
The Wittig reaction of (methallylidene)triphenylphosphorane with erythro-4-acetoxy-2,3-dimethylbutanal afforded erythro-2,3,6-trimethylhepta-4,6-dien-1-yl acetate as a mixture of E and Z isomers in a 85: 15 ratio...
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Article
Catalytic amination of polychloroarenes promoted by the Buchwald ligands
Palladium-catalyzed amination of 1,2,4,5-tetrachlorobenzene with morpholine or pyrrolidine in the presence of 2-dicyclohexylphosphino-2’-(dimethylamino)biphenyl (DavePhos, the Buchwald ligand) afforded the cor...
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Article
Asymmetric organocatalysis: from a breakthrough methodology to sustainable catalysts and processes
The evolution of modern catalytic methodologies for asymmetric organic synthesis, including transition metal and organocatalysis, is briefly considered. The results of the authors’ research group comprise the ...
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Article
Functionalized polychloroarenes in the Bichwald ligand-promoted Suzuki cross-coupling
Palladium-catalyzed Suzuki cross-coupling of isomeric dichloroacetophenones with phenylboronic acid in the presence of 2-dicyclohexylphosphino-2′-(dimethylamino)-biphenyl (DavePHOS, a Buchwald ligand) affords ...
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Article
Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands
The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversi...
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Article
Nitration of Alkenes and Oxiranes with Nitrogen(IV) Oxide in Liquid and Supercritical Carbon Dioxide Media
For the first time the reactions of radical nitration of alkenes and oxiranes with nitrogen dioxide in the liquid and supercritical carbon dioxide (sc-CO2) media were carried out. Using octene-1, styrene, and the...
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Article
Novel C2-symmetric phenylglycine derivatives as organocatalysts of the Michael reaction between nitroalkenes and ketones
A comprehensive study of the activity of the amide-type organocatalysts based on (R)- and (S)-phenylglycine and 1,2-di(2-pyridyl)-1,2-diaminoethane in the asymmetric Michael reaction between various nitroalkenes ...
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Article
Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts
Bifunctional C2-symmetric organocatalysts derived from chiral 1,2-diaminoethanes and (S)-2-aminomethylpyrrolidine were fi rst used for promoting the asymmetric Michael addition of aliphatic aldehydes to nitroalke...
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Article
Synthesis and structural investigation of 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide
The oxidation of hexane-2,3,4,5-tetraone tetraoxime with dinitrogen tetroxide was studied in different solvents. The primary furoxan ring closure was found to occur involving either two central or two terminal...
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Article
1,4-cis-Hydrogenation of butyl sorbate in supercritical carbon dioxide
Hydrogenation of butyl sorbate into butyl Z-hex-3-enoate in supercritical carbon dioxide proceeds at high conversion and selectivity of 93–96% under catalysis with chromium hexacarbonyl at 180 °C and on using (me...
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Article
Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release
A convenient one-pot synthesis of nitro derivatives of 2,1,3-benzothiadiazole 1-oxides by the reaction of o-nitroanilines with sulfur monochloride was developed. The structural features of 4-nitrobenzothiadiazole...
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Article
Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetr...
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Article
Unusual transformation of 3-alkylfuroxans into 3-(nitrooxyalkyl)furoxans on treatment with a mixture of nitric and sulfuric acids
A versatile one-pot synthesis of 4-substituted 3-(nitrooxyalkyl)furoxans by the reaction of 3-alkylfuroxans with a mixture of nitric and sulfuric acids was developed. A plausible mechanism of this unusual tran...
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Article
Relative permittivity of monocomponent and binary solutions of N2O5 in liquid CO2 and their activity in nitration of cellulose
Static relative permittivity of liquid carbon dioxide solutions of dinitrogen pentoxide and its mixtures with nitric, acetic or trifluoroacetic acids is measured. The procedure for nitration of cellulose acqui...
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Article
Detonation nanodiamond complexes with cancer stem cells inhibitors or paracrine products of mesenchymal stem cells as new potential medications
Combined use of complexes of the most active chemotherapeutic drugs and detonation nanodiamonds (DND) is a new trend in cancer therapy, which is probably related to selective chemotherapeutic drug delivery by ...
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Article
Synthesis, spectral properties, and conformations of nonlinear cross-conjugated polyenes containing pyrane or dihydropyridine fragment
New cross-conjugated ω,ω′-dimethylaminopolyenes containing the central pyrane or N-methyldihydropyridine fragment were synthesized. In new compounds, the interaction of the aminopolyene chromophores occurs throug...
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Article
Chiral Ionic Liquid/ESI-MS Methodology as an Efficient Tool for the Study of Transformations of Supported Organocatalysts
An efficient approach to the study of deactivation pathways of chiral organocatalysts in asymmetric Michael reactions by modifying original catalysts with ionic-liquid fragments followed by the electrospray io...
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Article
Organocatalysis of asymmetric aldol reaction in water: comparison of catalytic properties of (S)-valine and (S)-proline amides
(S)-Valine amides containing (S)- or (R)-α-phenylethyl substituents at N1 atom efficiently catalyze asymmetric aldol reactions between cyclic (heterocyclic) ketones and aromatic aldehydes in water, predominantly ...
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Article
Asymmetric organocatalysis: from proline to highly efficient immobilized organocatalysts
The recent results of the authors’ research group on the application of chiral ionic liquids and related compounds as recoverable organocatalysts of asymmetric reactions are reviewed.
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Article
Synthesis of cyclopropane-1,1,2,2-tetracarboxylic acid derivatives from aldehydes and CH-acids in the K2CO3/Bun 4NPF6/toluene heterogeneous system
A one-pot method for the synthesis of cyclopropane-1,1,2,2-tetracarboxylic derivatives was developed starting from aldehydes and cyanoacetic and 2-bromomalonic esters under heterogeneous conditions (K2CO3/PhMe) i...
