Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: Synthesis of trihalomethylated spiroindenepyrroli(zi)dines

[Display omitted] •Reactions of 3,3,3-trihalogeno-1-nitropropenes with stabilised azomethine ylides were studied.•A number of CX3-containing spiropyrrolidines and spiropyrrolizidines was obtained.•1,3-Cycloaddition proceeds with good efficiency and high regio- and stereoselectivity.•Major products of the reaction with proline ylides showed different regioselectivity from the products of β-nitrostyrenes. Reactions of (E)-3,3,3-trihalogeno-1-nitropropenes with stabilised azomethine ylides derived from ninhydrin and indenoquinoxalinones on the one hand, and sarcosine and proline on the other, proceed regio- and diastereoselectively to give a number of trihalomethylated spiroindenepyrrolidines and spiroindenepyrrolizidines in good yields.