Highly efficient synthesis of alpha-amino amidines from ynamides by the Cu-catalyzed three-component coupling reactions

Abstract

Using ynamides as one of the reacting components, the Cu-catalyzed three-component reaction of sulfonyl or phosphoryl azides and amines affords alpha-amino amidines in high yields under mild conditions. Synthetic utility of the produced compounds was demonstrated in the diastereoselective alkylation of alpha-amino amidines bearing a chiral oxazolidinone moiety. It was also shown that alpha-amino imidates could be readily prepared by employing alcohols instead of amines. (c) 2008 Elsevier Ltd. Ail rights reserved.