Chiral ScIII-N,N'-Dioxide-Catalyzed 1,3-Dipolar Cycloaddition of Diaziridines with Chalcones.

ABSTRACT

A highly enantioselective 1,3-dipolar cycloaddition of meso-diaziridines with chalcones was realized by utilizing the ScIII-N,N'-dioxide complex as the catalyst. In this transformation, the 1,3-dipole intermediates generated from the C-N bond cleavage of diaziridine were trapped by chiral N,N'-dioxide/scandium(III) complex activated chalcones to undergo enantioselective 1,3-dipolar cycloaddition. A range of chiral 1,5-diazabicylo[3.3.0]octane derivatives were readily synthesized in good yields with high diastereo- and enantioselectivities.