Iodide-Mediated [3 + 2]-Cycloaddition Reaction with N-Tosylaziridines and α,ß-Unsaturated Ketones.

The [3 + 2]-cycloaddition reaction between N-tosylaziridines and α,ß-unsaturated ketones was promoted with lithium iodide. The reaction proceeded under mild conditions to provide N-tosylpyrrolidines. Quaternary carbon-possessing 3,3-disubstituted pyrrolidines including spiro compounds were afforded in high yields. A simple procedure with easy to handle reagents makes this reaction concise. The intramolecular version of this reaction was applied to synthesize tropane skeletons.