Stereoselective Synthesis of Hydroxy Diamino Acid Derivatives and the Caprolactam Unit of Bengamide A through Organocatalytic -Hydroxylation and Reductive Amination of Aldehydes

摘要

The synthetic utility of proline-catalyzed asymmetric -hydroxylation and subsequent reductive amination of aldehydes to afford chiral -amino alcohols is explored for the first time. Stereoselective synthesis of orthogonally protected 5-hydroxylysine, 4-hydroxyornithine and 2,4-diamino-3-hydroxybutanoic acid was achieved. (2S,5S)-5-Hydroxylysine synthesized in this way was converted into the aminocaprolactam ring system of bengamide A.