Diastereoselective cycloadditions involving methyleneaziridines: Reactions with tetracyanoethylene

Article abstract of DOI:10.1016/S0040-4039(99)01267-8

2-Methyleneaziridines 2a-e containing a stereogenic centre on the N- substitutent undergo [2π+2π] cycloadditions with tetracyanoethylene to produce diastereomeric 5-azaspiro[3.2]hexanes 3a-e and 4a-e in moderate to good yields (32-82%). The diastereoselectivity of these cycloadditions (12- 68% de) is shown to be dependent on the nature of the N-substitutent. The structure of 5-azaspiro→3.2]hexane 4a has been unambiguously determined by X-ray crystallography.