Giovanna Dettori

Synthesis of new oxazole-containing peptidomimetics

Abstract Enantiospecific syntheses of optically active amino acids containing an oxazole moiety are described. Two different strategies for their insertion in a peptidomimetic chain are also discussed. The procedures presented are based on materials readily available in multigram quantities.

BH3-promoted stereoselective β-lithiation of N-alkyl-2-phenylaziridines.

BH(3) complexes of N-alkyl-2-phenylaziridines have been synthesized and their structure and stereochemistry proved with DFT calculations and NMR experiments. It has been demonstrated that the Lewis acid complexation is able to promote a regioselective β-lithiation in 2-phenylaziridino-borane complexes. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstituted aziridines.

A two-step tandem reaction to prepare hydroxamic acids directly from alcohols

The first synthesis of hydroxamic acids from alcohols has been developed. Both benzylic and aliphatic alcohols can be tolerated and applied in this reaction. The methodology is economical, environmentally benign and high yielding.

Benzylic Organometals via Reductive Metalation Procedures

The review discusses two different reductive metalation approaches to the generation of benzylic organometals. In the first part, the scope of the generation of polar benzylic organometals by the reductive cleavage of carbon - heteroatom sigma bonds will be presented. Besides briefly showing the evolution of the technique, the review deals with recent achievements in the generation of benzylic derivatives of alkali metals by the reductive cleavage of carbon - halogen, carbon - oxygen, carbon - nitrogen and carbon - sulphur bonds. Significant synthetic applications of this procedure are described, showing that an appropriate choice of reaction conditions (solvent, temperature, alkali metal, employment of an electron shuttle) strongly affects the outcome of the cleavage reaction. In the second part, the application of the reductive metalation to carbon - carbon, carbon - oxygen and carbon - nitrogen double bonds is described, a procedure leading to the generation of vic-diorganometallic derivatives. Synthetic applications of these diorganometals are illustrated, underlining the possible application of 1,2-diarylsubstituted vic-dicarbanions as synthetic analogues of an activated form of an alkali metal that, however, function under homogeneous and mild reaction conditions.

Active-alkali metal-promoted reductive cleavage of chlorinated phenols

We investigated the degradation of chlorinated phenols under reductive electron transfer reaction conditions. Although Li and Na metal proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Additionally, efficient dehalogenation of the sodium salts of several mono-, di-, and tri-chlorophenols was obtained by their reduction with an excess of Na metal and a catalytic amount of naphthalene.Graphical Abstract.

Microwave‐Assisted Carbamoylation of Amines

Abstract The influence of microwave irradiation on the reaction of various amines with benzyl chloroformate and di‐tert‐butyl dicarbonate was investigated. Microwave irradiation was successfully applied to the carbamoylation of several nonfunctionalized and functionalized amines, including amino acids and nucleobases, leading to satisfactory to high product conversion within very short reaction times.