Abstract
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.
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