Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters.
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...
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doaj-7dfdae62614e42498e3fa7f83dc0793c2020-11-25T01:25:03ZengPublic Library of Science (PLoS)PLoS ONE1932-62032013-01-0181e5323110.1371/journal.pone.0053231Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters.Paula Pérez-FaginasM Teresa ArandaM Teresa García-LópezLourdes InfantesAsia Fernández-CarvajalJosé Manuel González-RosAntonio Ferrer-MontielRosario González-Muñiz1,2-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.http://europepmc.org/articles/PMC3538761?pdf=render |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Paula Pérez-Faginas M Teresa Aranda M Teresa García-López Lourdes Infantes Asia Fernández-Carvajal José Manuel González-Ros Antonio Ferrer-Montiel Rosario González-Muñiz |
spellingShingle |
Paula Pérez-Faginas M Teresa Aranda M Teresa García-López Lourdes Infantes Asia Fernández-Carvajal José Manuel González-Ros Antonio Ferrer-Montiel Rosario González-Muñiz Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. PLoS ONE |
author_facet |
Paula Pérez-Faginas M Teresa Aranda M Teresa García-López Lourdes Infantes Asia Fernández-Carvajal José Manuel González-Ros Antonio Ferrer-Montiel Rosario González-Muñiz |
author_sort |
Paula Pérez-Faginas |
title |
Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
title_short |
Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
title_full |
Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
title_fullStr |
Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
title_full_unstemmed |
Highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
title_sort |
highly functionalized 1,2-diamino compounds through reductive amination of amino acid-derived β-keto esters. |
publisher |
Public Library of Science (PLoS) |
series |
PLoS ONE |
issn |
1932-6203 |
publishDate |
2013-01-01 |
description |
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. |
url |
http://europepmc.org/articles/PMC3538761?pdf=render |
work_keys_str_mv |
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