Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters

• Published in: PloS one 2013, Vol.8 (1), p.e53231-e53231
• Main Authors: Pérez-Faginas, Paula, Aranda, M Teresa, García-López, M Teresa, Infantes, Lourdes, Fernández-Carvajal, Asia, González-Ros, José Manuel, Ferrer-Montiel, Antonio, González-Muñiz, Rosario
• Format: Article
• Language: English
• Subjects: Acids; Amination; Amines; Amino acids; Amino Acids - chemistry; Chemistry; Crystal structure; Crystallography, X-Ray; Derivatives; Diamines - chemistry; Diastereoisomers; Esters; Esters - chemistry; Heterocyclic compounds; Hydrogenation; Models, Molecular; Oxidation-Reduction; Peptides; Reagents; Reducing agents; Reducing Agents - chemistry; RNA polymerase; Stereoisomerism; Stereoselectivity; Studies; Transformation
• ISSN: 1932-6203; 1932-6203
• DOI: 10.1371/journal.pone.0053231

1,2-Diamine derivatives are valuable building blocks to heterocyclic compounds and important precursors of biologically relevant compounds. In this respect, amino acid-derived β-keto esters are a suitable starting point for the synthesis of β,γ-diamino ester derivatives through a two-step reductive amination procedure with either simple amines or α-amino esters. AcOH and NaBH(3)CN are the additive and reducing agents of choice. The stereoselectivity of the reaction is still an issue, due to the slow imine-enamine equilibria through which the reaction occurs, affording mixtures of diastereoisomers that can be chromatographically separated. Transformation of the β,γ-diamino esters into pyrrolidinone derivatives allows the configuration assignment of the linear compounds, and constitutes an example of their potential application in the generation of molecular diversity.