Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts
- PMID: 20359172
- PMCID: PMC2862278
- DOI: 10.1021/ol1005104
Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts
Abstract
Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.
References
-
-
For recent reviews on hydrogen-bond donor catalysis, see: Doyle AG, Jacobsen EN. Chem Rev. 2007;107:5713–5743.McGilvra JD, Gondi VB, Rawal VH. In: Enantioselective Organocatalysis. Dalko PI, editor. Wiley-VCH; Weinheim: 2007. pp. 189–254.Yu X, Wang W. Chem Asian J. 2008;3:516–532.
-
-
- Huang Y, Unni AK, Thadani AN, Rawal VH. Nature. 2003;424:146. - PubMed
- Thadani AN, Stankovic AR, Rawal VH. Proc Natl Acad Sci USA. 2004;101:5846–5850. - PMC - PubMed
- McGilvra JD, Unni AK, Modi K, Rawal VH. Angew Chem Int Ed. 2006;45:6130–6133. - PubMed
- Gondi VB, Hagihara K, Rawal VH. Angew Chem Int Ed. 2009;48:776–779. - PMC - PubMed
-
-
Since the first publication from our laboratory in 2008, other reports of squaramide-based organocatalysts have appeared: Cheon CH, Yamamoto H. Tetrahedron Lett. 2009;50:3555–3558.Lee JW, Ryu TH, Oh JS, Bae HY, Jang HB, Song CE. Chem Commun. 2009:7224–7226.
-
-
- Greck C, Genêt JP. Synlett. 1997:741–748.
- Genet JP, Greck C, Lavergne D. In: Modern Amination Methods. Ricci A, editor. Wiley-VCH; Weinheim: 2000. pp. 65–102.
- Dembech P, Seconi G, Ricci A. Chem Eur J. 2000;6:1281–1286. - PubMed
- Duthaler RO. Angew Chem Int Ed. 2003;42:975–978. - PubMed
- Greck C, Drouillat B, Thomassigny C. Eur J Org Chem. 2004:1377–1385.
- Erdik E. Tetrahedron. 2004;60:8747–8782.
- Janey JM. Angew Chem Int Ed. 2005;44:4292–4300. - PubMed
- Nair V, Biju AT, Mathew SC, Babu BP. Chem Asian J. 2008;3:810–820. - PubMed
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