650596-81-9Relevant academic research and scientific papers
Preparation of syn-δ-Hydroxy-β-amino Esters via an Intramolecular Hydrogen Bond Directed Diastereoselective Hydrogenation. Total Synthesis of (3S,4aS,6R,8S)-Hyperaspine
Zhu, Wei,Ma, Dawei
, p. 5063 - 5066 (2003)
(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.
