Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides
- PMID: 14535766
- PMCID: PMC2897059
- DOI: 10.1021/ol035647d
Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides
Abstract
[reaction: see text] A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.
References
-
-
For reviews of the chemistry of ynamines and ynamides, see: Mulder JA, Kurtz KCM, Hsung RP. Synlett. 2003:1379. Zificsak CA, Mulder JA, Hsung RP, Rameshkumar C, Wei L-L. Tetrahedron. 2001;57:7575. Himbert G. In: Methoden der Organischen Chemie (Houben-Weyl) Part 3. Kropf H, Schaumann E, editors. Vol. E15. Stuttgart: Georg Thieme Verlag; 1993. pp. 3267–3443. Collard-Motte J, Janousek Z. Top. Curr. Chem. 1986;130:89.
-
-
- Hsung RP, Zificsak CA, Wei L-L, Douglas CJ, Xiong H, Mulder JA. Org. Lett. 1999;1:1237.
- Witulski B, Stengel T. Angew. Chem., Int. Ed. 1999;38:2426. - PubMed
- Witulski B, Stengel T, Fernández-Hernández JM. J. Chem. Soc., Chem. Commun. 2000:1965.
- Witulski B, Alayrac C. Angew. Chem., Int. Ed. 2002;41:3281. - PubMed
- Witulski B, Lumtscher J, Bergsträsser U. Synlett. 2003:708.
-
- Witulski B, Buschmann N, Bergsträsser U. Tetrahedron. 2000;56:8473.
- Minière S, Cintrat J-C. Synthesis. 2001;5:705.
- Minière S, Cintrat J-C. J. Org. Chem. 2001;66:7385. - PubMed
- Timbart L, Cintrat J-C. Chem. Eur. J. 2002;8:1637. - PubMed
- Mulder JA, Kurtz KCM, Hsung RP, Coverdale H, Frederick MO, Shen L, Zificsak CA. Org. Lett. 2003;5:1547. - PubMed
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