A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions.

ABSTRACT: Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives.

SUBMITTER: Zahoor AF 

PROVIDER: S-EPMC3182440 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature