Formation of Optically Pure Cyclic Amines by Intramolecular Conjugate Displacement

Intramolecular conjugate displacement (ICD) has been applied to the Morita–Baylis–Hillman adducts formed from (5S)-5-(l-menthyloxy)-2­(5H)-furanone and aldehydes that carry a protected β- or γ-amino group. DIBAL-H reduction of the resulting ICD products releases optically pure six- or seven-membered cyclic amines having a stereogenic center α to nitrogen.