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

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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.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2008-03
Language
English
Article Type
Article
Keywords

CHIRAL YNAMIDES; AMIDE SYNTHESIS; N-ALKYNYLATION; SULFONYL AZIDE; CYCLOADDITIONS; TRIAZOLES; CHEMISTRY; PEPTIDES; LIGANDS; ALKYNE

Citation

TETRAHEDRON LETTERS, v.49, no.11, pp.1745 - 1749

ISSN
0040-4039
DOI
10.1016/j.tetlet.2008.01.073
URI
http://hdl.handle.net/10203/88099
Appears in Collection
CH-Journal Papers(저널논문)
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