The cyanobis(dibenzylamino)borane-mediated transformation of chiral aldehydes into the corresponding alpha-amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2-diamines and hydroxylated alpha-amino acids that are of interest as core key units of biologically active substances or as potential ligands for asymmetric catalysis. The stereochemical outcome of the aminative cyanation reaction is discussed.
Towards the Synthesis of Highly Functionalized Chiral alpha-Amino Nitriles by Aminative Cyanation and Their Synthetic Applications / Bernardi, Luca; Bonini, Bianca F.; Capitò, Elena; Comes Franchini, Mauro; Dessole, Gabriella; Fini, Francesco; Fochi, Mariafrancesca; Herrera, Raquel P.; Ricci, Alfredo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2006:1(2006), pp. 207-217. [10.1002/ejoc.200500501]
Towards the Synthesis of Highly Functionalized Chiral alpha-Amino Nitriles by Aminative Cyanation and Their Synthetic Applications
FINI, Francesco;
2006
Abstract
The cyanobis(dibenzylamino)borane-mediated transformation of chiral aldehydes into the corresponding alpha-amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2-diamines and hydroxylated alpha-amino acids that are of interest as core key units of biologically active substances or as potential ligands for asymmetric catalysis. The stereochemical outcome of the aminative cyanation reaction is discussed.
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