Towards the Synthesis of Highly Functionalized Chiral alfa-Amino Nitriles via Aminative Cyanation and their Synthetic Applications
Luca Bernardi, Bianca F. Bonini, Elena Capitò, Mauro Comes-Franchini, Gabriella Dessole, Francesco Fini, Mariafrancesca Fochi, Raquel P. Herrera, Alfredo Ricci. Towards the Synthesis of Highly Functionalized Chiral alfa-Amino Nitriles via Aminative Cyanation and their Synthetic Applications. Eur. J. Org. Chem.. 2006, Vol. , p. 207-2006.
<p>The cyanobis(dibenzylamino)borane-mediated transformation of chiral aldehydes into the corresponding alfa-amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2-diamines and hydroxylated alfa-amino acids that are of interest as core key unitsof biologically active substances or as potential ligands for asymmetric catalysis. The stereochemical outcome of the aminative cyanation reaction is discussed.</p>
<p>The cyanobis(dibenzylamino)borane-mediated transformation of chiral aldehydes into the corresponding alfa-amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2-diamines and hydroxylated alfa-amino acids that are of interest as core key unitsof biologically active substances or as potential ligands for asymmetric catalysis. The stereochemical outcome of the aminative cyanation reaction is discussed.</p>