A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

Michael O Frederick; Jason A Mulder; Michael R Tracey; Richard P Hsung; Jian Huang; Kimberly C M Kurtz; Lichun Shen; Christopher J Douglas

doi:10.1021/ja021304j

A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

J Am Chem Soc. 2003 Mar 5;125(9):2368-9. doi: 10.1021/ja021304j.

Authors

Michael O Frederick¹, Jason A Mulder, Michael R Tracey, Richard P Hsung, Jian Huang, Kimberly C M Kurtz, Lichun Shen, Christopher J Douglas

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

PMID: 12603105
DOI: 10.1021/ja021304j

Abstract

A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.