Chiral ScIII-N,N'-Dioxide-Catalyzed 1,3-Dipolar Cycloaddition of Diaziridines with Chalcones
Haipeng Hu1, Jinxiu Xu1, Fang Wang1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
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.
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