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

α-Amino amidines were efficiently prepared by the Cu-catalyzed three-component coupling of ynamides, sulfonyl or phosphory azides, and amines under mild conditions. Using ynamides as one of the reacting components, the Cu-catalyzed three-component reaction of sulfonyl or phosphoryl azides and amines...

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Bibliographic Details
Published in:Tetrahedron letters 2008-03, Vol.49 (11), p.1745-1749
Main Authors: Kim, Ji Young, Kim, Seok Hwan, Chang, Sukbok
Format: Article
Language:English
Subjects:
Copper catalysis
Three-component reactions
Ynamides
α-Amino amidines
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Summary:α-Amino amidines were efficiently prepared by the Cu-catalyzed three-component coupling of ynamides, sulfonyl or phosphory azides, and amines under mild conditions. Using ynamides as one of the reacting components, the Cu-catalyzed three-component reaction of sulfonyl or phosphoryl azides and amines affords α-amino amidines in high yields under mild conditions. Synthetic utility of the produced compounds was demonstrated in the diastereoselective alkylation of α-amino amidines bearing a chiral oxazolidinone moiety. It was also shown that α-amino imidates could be readily prepared by employing alcohols instead of amines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.01.073