A short synthesis of azasugars via aldol reaction of chelated amino acid ester enolates

Article abstract of DOI:10.1016/S0040-4039(97)10176-9

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.