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Preparation of sugar-derived 1,2-diamines via indium-catalyzed aza-Henry-type reaction: application to the synthesis of 6-amino-1,6-dideoxynojirimycin
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Apr2013, Vol. 54 Issue 17, p2156-2159. 4p. - Publication Year :
- 2013
-
Abstract
- Abstract: The combination of (p-methoxyphenyl)imine, a bromonitroalkane, and zinc in the presence of catalytic indium allows straightforward access to β-nitroamine derivatives. The use of chiral sugar-derived imines furnished the corresponding β-nitroamines in high yields and stereoselectivities, from which the corresponding 1,2-diamines were easily obtained. The synthetic utility of the sugar-derived 1,2-diamines in the preparation of iminosugars was illustrated in a concise synthesis of 6-amino-1,6-dideoxynojirimycin. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 54
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 86369861
- Full Text :
- https://doi.org/10.1016/j.tetlet.2013.02.041