A Short Synthesis of Azasugars via Aldol Reaction of Chelated Amino Acid Ester Enolates

Autor: Grandel, Roland, Kazmaier, Uli
Zdroj: Tetrahedron Letters; January 1997, Vol. 38 Issue: 46 p8009-8012, 4p
Abstrakt: Aldol reactions of chelated amino acid ester enolates with chiral aldehydes gives rise to polyhydroxylated amino acids in a highly stereoselective fashion. These oxygenated amino acids can be converted into polyhydroxylated pipecolinic acids and azasugars by cyclization using the Mitsunobu reaction. A interesting epimerization was observed during the cyclization. © 1997 Elsevier Science Ltd.
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