ol9b04007_si_001.pdf (12.3 MB)
Chiral ScIII–N,N′‑Dioxide-Catalyzed 1,3-Dipolar Cycloaddition of Diaziridines with Chalcones
journal contribution
posted on 2019-12-13, 16:50 authored by Haipeng Hu, Jinxiu Xu, Fang Wang, Shunxi Dong, Xiaohua Liu, Xiaoming FengA 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.