Addition of carbon nucleophiles to cyclic N-acyliminium ions in SDS/water

The acid-catalyzed addition of 1,3-dicarbonyl compounds and activated olefins (silyl enol ethers and ethyl vinyl ether) to N-Boc-2-methoxypyrrolidine (1a) and N-Boc-2-methoxypiperidine (1b) in SDS/water medium is described. Good yields of the corresponding 2-substituted N-Boc pyrrolidines were generally observed from 1a while moderate yields prevailed from 1b.