Unexpected products from the attempted organolithium-mediated conversion of β-methoxy aziridines into allylic amines

Article abstract of DOI:10.1016/j.tetlet.2009.11.059

The organolithium-mediated conversion of cyclic trans-β-methoxy aziridines and cis-β-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-β-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established.