Daniele Muroni

Chiral phenanthrolines as ligands for Cu(I)-catalyzed asymmetric allylic oxidation

A number of chiral 1,10-phenanthrolines (phens) have been assessed in asymmetric Cu(I)-catalyzed allylic oxidation of cyclohexene. Very effective copper-phen catalysts are obtained only when these ligands bear at least a substituent close to the reactive site of the catalyst. Enantioselectivity up to 36% was obtained.

Chiral 2-(2-phenylthiophenyl)-5,6,7,8-tetrahydroquinolines: new N-S ligands for asymmetric catalysis - Palladium-catalyzed allylic alkylation and copper-catalyzed cyclopropanation reactions

Diastereomeric pure 2-(2-phenylthiophenyl)-5,6,7,8-tetrahydroquinolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate and in the copper-catalyzed cyclopropanation of styrene with ethyldiazoacetate. Enantioselectivity up to 63% was obtained.

Chiral thienylpyridines as N–S ligands for asymmetric catalysis: Palladium-catalyzed allylic alkylation and copper-catalyzed cyclopropanation reactions

Diastereomeric pure thienylpyridines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate and copper-catalyzed cyclopropanation of styrene with ethyl diazoacetate. These ligands provided unreactive palladium catalysts but effective copper catalysts affording however low enantioexcesses.

Efficient syntheses of 1-azatricyclic ring systems from anthranylamide

Concise syntheses of novel tricyclic quinazolinone and pyrrolo benzoazacyclononenone alkaloids in two and three steps (two pots), starting from 3-styryl quinazolinone, by utilizing RCM and cascade spiro-to fused protocols, respectively, were reported.

(Z,1S,10aR)-(−)-Menthyl 1-hy­droxy-1,2,3,5,6,7,10,10a-octa­hydro­pyrrolo­[1,2-a]azocine-10a-carboxyl­ate

The structure determination confirms the stereochemistry of the title compound, C21H35NO3, obtained as an intermediate in the enantioselective synthesis of deoxynojirimicine analogs. The system contains a pyrrolo[1,2-a]azocine backbone, which was synthesized by a domino process involving a [2,3]-sigmatropic rearrangement. The incorporation of a chiral auxiliary (−)-menthyl, whose stereocentres are not involved during the synthesis, enables the assignation of absolute configuration. The crystal structure features O—H⋯O hydrogen bonds involving the hydroxy groups as donors and the carbonyl groups as acceptors, which link the molecules into chains running along [010].