The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanols

The reaction between racemic acyl chlorides and racemic trans-2-substituted-cyclohexanols proceeds diastereoselectively. We found for the first time that addition of a tertiary amine not only accelerates the acylation, but for some substituents leads to complete inversion of diastereoselectivity. These observations have been rationalized in terms of a possible stereoselective intramolecular assistance by the substituent group during the acylation of the neighboring hydroxyl group

Syntheses of small cluster oligosaccharide mimetics

We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) - potential glycosidase inhibitors - to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2- cyclohexanedicarboxylic acids

Arylsulfanyl-alkyl alcohols as chiral auxiliaries

We report a novel type of chiral auxiliaries based on a transformation of chiral arylsulfanyl-alkyl alcohols into cyclic sulfonium ions and a stereoselective nucleophilic cleavage of the latter

Arylsulfanyl-alkyl alcohols as chiral auxiliaries

We report a novel type of chiral auxiliaries based on a transformation of chiral arylsulfanyl-alkyl alcohols into cyclic sulfonium ions and a stereoselective nucleophilic cleavage of the latter

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur

CONVENIENT SYNTHESIS OF NEW 1,10-PHENANTHROLINE LIGANDS AND THE DEPENDENCE OF THEIR CONFORMATIONS ON COMPLEXATION

Derivatives of phenanthroline are widely used in analytical and inorganic chemistry as ligands for complexation of heavy metals. In particular, they bind cations of heavy metals in the processes of the industrial wastewater purification

CONVENIENT SYNTHESIS OF 1,3-DITHIOLANE-2-THIONES

Trithiocarbonates (1,3-dithiolane-2-thiones, 2) are used as building blocks in synthesis of versatile ligands and polymers. They also possess radioprotective and insecticidal activities

CONVENIENT SYNTHESIS OF NEW 1,10-PHENANTHROLINE LIGANDS AND THE DEPENDENCE OF THEIR CONFORMATIONS ON COMPLEXATION

Derivatives of phenanthroline are widely used in analytical and inorganic chemistry as ligands for complexation of heavy metals. In particular, they bind cations of heavy metals in the processes of the industrial wastewater purification

CONVENIENT SYNTHESIS OF 1,3-DITHIOLANE-2-THIONES

Trithiocarbonates (1,3-dithiolane-2-thiones, 2) are used as building blocks in synthesis of versatile ligands and polymers. They also possess radioprotective and insecticidal activities