Alberto Morreale

Reagent-controlled diastereoselective aminations with a new chiral nosyloxycarbamate

The synthesis of a new chiral nosyloxycarbamate derived from Helmchens auxiliary is described. Reactions performed with this aminating reagent successfully give the formation of diastereomeric allylic carbamates or diastereomeric aziridines starting from different kinds of olefins.

Direct amination of β-oxo esters

Abstract The reaction of NsONHCO 2 Et, in the presence of CaO, with β-oxo esters gives the corresponding aminated products in yields up to 58%. A substrate carrying the Oppolzer sultam undergoes amination with 40% diastereoselectivity.

Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides

Abstract Starting from a library of 2-l-α-amino acyl (E)-acrylonitriles, different short 2-cyano and 2-amido aziridinyl peptides, potential protease inhibitors, were obtained under parallel solution-phase conditions. The transformations include careful selection of conditions for aziridine deprotection and cyano group partial hydrolysis.

Aziridination of 2-(Phenylsulfinyl)-2-cycloalkenones with Arylsulfonyloxycarbamates

Highly functionalised aziridines are easily obtained with high levels of diastereoselectivity (up to 98%) from 2-(phenylsulfinyl)-2-cycloalkenones by treatment with arylsulfonyloxycarbamates in the presence of bases under mild conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)

Functionalised enones as starting materials for the construction of aziridine scaffolds

Abstractα-Substituted β-keto esters have been transformedby means of a straightforward procedure into aziridine-1,2-dicarboxylates, which have been efficiently converted into alkenyl aziridine-1,2-dicarboxylates through Wittig olefination reaction. The possibility of aziridine ring elaborations and the presence of an olefin function make these new molecules suitable scaffolds for further derivatisation into potential bioactive targets.