(Equation presented) Hydrogenation of δ-hydroxy-β-ketoester- derived enamines 8 produces syn-δ-hydroxy-β-amino esters 9 diastereoselectively, which may be directed by the formation of an intramolecular hydrogen bond between the δ-hydroxyl and β-amino groups. By using this method and a Dieckmann reaction as the key steps, (3S,4aS,6R,8S)-hyperaspine, a new type of ladybird alkaloid, is synthesized.