Abstract
β-amino acid esters are important scaffolds in medicinal chemistry and valuable building blocks for materials synthesis. Surprisingly, the waste-free construction of such moieties from readily available or renewable starting materials has not yet been addressed. Here we report on a robust and versatile method for obtaining β-amino acid esters by direct amination of β-hydroxyl acid esters via the borrowing hydrogen methodology using a cooperative catalytic system that comprises a homogeneous ruthenium catalyst and an appropriate Brønsted acid additive. This method allows for the direct amination of esters of 3-hydroxypropionic acid, a top value-added bio-based platform chemical, opening a simple route to access β-amino acid esters from a range of renewable polyols including sugars and glycerol.
Highlights
Β-amino acid esters are important scaffolds in medicinal chemistry and valuable building blocks for materials synthesis
3-Hydroxypropionic acid (3-HP) has been identified as one of the top twelve value-added renewable platform chemicals[11,12,13], there is a clear demand for its diversification beyond already existing targets[11,12,13,14]
We developed the first N-alkylation of unprotected α-amino acids with alcohols using the Ru-based Shvo’s catalyst[33]. This robust and base-free catalytic system appeared as excellent starting point for the synthesis of β-amino acid esters from β-hydroxyl acid esters and various amines (Fig. 1b)
Summary
Β-amino acid esters are important scaffolds in medicinal chemistry and valuable building blocks for materials synthesis. We report on a robust and versatile method for obtaining β-amino acid esters by direct amination of βhydroxyl acid esters via the borrowing hydrogen methodology using a cooperative catalytic system that comprises a homogeneous ruthenium catalyst and an appropriate Brønsted acid additive. This method allows for the direct amination of esters of 3-hydroxypropionic acid, a top value-added bio-based platform chemical, opening a simple route to access β-amino acid esters from a range of renewable polyols including sugars and glycerol. In the recent pioneering work, Yan and coworkers have reported the first example of catalytic amination of
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