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 and Christopher J. Douglas

*Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, Email: rphsungpharmacy.wisc.edu

M. O. Frederick, J. A. Mulder, M. R. Tracey, R. P. Hsung, J. Huang, K. C. M. Kurtz, L. Shen, C. J. Douglas, J. Am. Chem. Soc., 2003, 125, 2368-2369.

DOI: 10.1021/ja021304j (free Supporting Information)

---

Abstract

A copper-catalyzed direct N-alkynylation of amides has been developed leading to a facile entry for syntheses of chiral ynamides.

see article for more examples

---

---

Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides

X. Zhang, Y. Zhang, J. Huang, R. P. Hsung, K. C. M. Kurtz, J. Oppenheimer, M. E. Petersen, I. K. Sagamanova, L. Shen, M. R. Tracey, J. Org. Chem., 2006, 71, 4170-4177.

---

Key Words

Ynamides

---

ID: J48-Y2003-1320