Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals

Article abstract of DOI:10.1016/S0040-4020(97)00161-0

Optically active cyclohex-3-en-1-one ketals by photolysis of N₃CO₂-Et or N₃C(OEt)NMs or by CaO induced α-elimination of NsONHCO₂Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-β-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of (R)-2-aminoadipic acid.