The formation of 1 out of 64 stereoisomers, i.e. controlling the creation of 6 stereocenters, of important optically active bicyclo[3.3.1]non-2-ene compounds, has been achieved using organocatalysis; the reaction proceeds with excellent stereocontrol and can be carried out with the generation of enantiopure products using chromatography-free procedures.

Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropone derivatives was developed. Up to 97% ee was obtained for the chiral dinucleus BINOL-aluminum complex catalyzed reaction between tropones and ketene diethyl acetal to give bicyclo[3.2.2] ring structures, which opens up a unique way of making chiral seven-membered rings.

Density functional theory computations at the B3LYP/6-31G(d,p) level have been carried out for three types of model compounds, viz. (i) 4-substituted bicyclo[2.2.2]octane carboxylic acids, (ii) anions of 4-substituted bicyclo[2.2.2]octane carboxylic acids and (iii) 4-substituted quinuclidines where the substituents are NO(2), CN, Cl, Br, CF(3), F, CHO, CH(2)Cl, COOH, COCH(3), CONH(2), OH, OCH(3...

This highlight review describes the recent development of an electrophile-triggered 1,2-metallate rearrangement organoboronic ester ate-complex, which proceeds through 1,2-difunctionalization carbon–carbon σ- and π-bonds, using strain energy as a driving force. Coupling reactions small ring carbocyclic boronic esters, such cyclopropyl-, bicyclo[1.1.0]butyl-, cyclopropenyl-boronic ester, are sum...

Treatment of aryl-fused bicyclo[4.2.0]octanols with an oxidant such as phenyliodine diacetate (PIDA) or hypochlorous acid gave dihydrofuran-containing polycyclic aromatic compounds by selective β-cleavage the cyclobutanol moiety. Mechanistic studies suggest that oxygen atom hydrofuran ring is incorporated from hydroxy group substrate via intramolecular addition. The oxidative transformation sho...

Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.

Fluoroquinolones are an important class of modern and efficient antibacterial drugs with a broad spectrum of activity. Levofloxacin (the optically active form of ofloxacin) is one of the most promising fluoroquinolone drugs, and its antibacterial activity is substantially higher than the activity of other drugs of the fluoroquinolone family. Earlier, in the Postovsky Institute of Organic Synthe...

A one-pot metathetic ring opening of substituted bicyclo[3.2.0]heptenones to linear polyene ketones is described. The reaction proceeds with conservation of the endocyclic (Z)-double bond. Exo-substituted vinylcyclobutanones result in (4Z,6E)-configured trienones, while endo-substituted phenyl derivatives generate (4Z,6Z)-configured dienones.