An organocatalytic asymmetric domino [3+2]-cycloaddition-acyl transfer reaction between in situ generated azomethine ylides and α-nitro-α,β-unsaturated ketones has been developed.

Abstract

Herein we have developed an organocatalytic asymmetric domino [3+2]-cycloaddition-acyl transfer reaction between in situ generated azomethine ylides and α-nitro-α,β-unsaturated ketones. The desired penta-substituted pyrrolidine products were obtained in high yields and in moderate to good enantio- and diastereoselectivities. Also, an isomerization reaction in silica gel was performed for the formation of another diastereomer in high yields with retention of enantioselectivities.