title: Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters.
abstract: 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.
authors: Instituto de Química-Médica, IQM-CSIC, Madrid, Spain.
authors: Paula
authors: P
authors: Pérez-Faginas
authors: M Teresa
authors: MT
authors: Aranda
authors: M Teresa
authors: MT
authors: García-López
authors: Lourdes
authors: L
authors: Infantes
authors: Asia
authors: A
authors: Fernández-Carvajal
authors: José Manuel
authors: JM
authors: González-Ros
authors: Antonio
authors: A
authors: Ferrer-Montiel
authors: Rosario
authors: R
authors: González-Muñiz
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003959:Diamines / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D019163:Reducing Agents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003959:Diamines; D004952:Esters; D019163:Reducing Agents