A Short Synthesis of Polyhydroxylated Piperidines by Aldol Reaction of Chelated Amino Acid Ester Enolates

✍ Scribed by Uli Kazmaier; Roland Grandel

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 432 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199809)1998:9<1833::aid-ejoc1833>3.0.co;2-f

✦ Synopsis

Aldol reactions of a chelated glycine ester enolate with a azasugars by cyclization using the Mitsunobu reaction. An interesting epimerization was observed during the chiral aldehyde gives rise to the corresponding polyhydroxylated amino acid with excellent induced cyclization. The potential glycosidase inhibitor 1deoxyaltronojirimycin (8b) was synthesized by this approach diastereoselectivity. These oxygenated amino acids can be converted into polyhydroxylated pipecolinic acids and in a highly stereoselective fashion.