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Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived ?-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 ?-keto esters are a suitable starting point for the synthesis of ?,?-diamino ester derivatives through a two-step reductive amination procedure with either simple amines or ?-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 ?,?-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.

SUBMITTER: Perez-Faginas P 

PROVIDER: S-EPMC3538761 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Pérez-Faginas Paula P   Aranda M Teresa MT   García-López M Teresa MT   Infantes Lourdes L   Fernández-Carvajal Asia A   González-Ros José Manuel JM   Ferrer-Montiel Antonio A   González-Muñiz Rosario R  

PloS one 20130107 1

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  ...[more]

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