Towards the synthesis of highly functionalized chiral α-amino nitriles by aminative cyanation and their synthetic applications

Abstract

The cyanobis(dibenzylamino)borane-mediated transformation of chiral aldehydes into the corresponding α-amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2-diamines and hydroxylated α-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. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.