A highly enantioselective 1,3-dipolar cycloaddition of α-substituted diazoesters with exocyclic enones was achieved with chiral scandium(Ⅲ)/N,N\'-dioxide complex as the catalyst.This protocol provided a facile and efficient route to optically active 1-pyrazoline-based spirochromanones and others with good outcomes(up to 97％yield,98％ee with＞95:5 dr).Moreover,enantioenriched 2-pyrazoline-based spirochromanones were also accessible by switching α-substituted diazoesters to α-dia-zoacetates.The further specific transformations of chiral pyrazoline-based spiro-compounds to spirocyclopropane derivatives were disclosed as well.