ChemInform Abstract: A Facile Transformation of the δ-Hydroxy-α-amino Lactones from α-Furfuryl Amide.

✍ Scribed by L.-X. LIAO; W.-S. ZHOU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 41 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199904186

✦ Synopsis

A Facile Transformation of the δ-Hydroxy-α-amino Lactones from α-Furfuryl Amide. -(S)-(I) and (R)-α-furfuryl amides, obtained previously by kinetic resolution using a modified Sharpless asymmetric epoxidation, are transformed into four enantiomeric δ-hydroxy-α-aminolactones, e.g. derivatives (V) and (IX), in 35 to 38% overall yield, involving Sharpless asymmetric dihydroxylation as the key step. Additionally, a more efficient method for the preparation of enantiomer (V) is described using the addition of a Grignard reagent to chiral aldimine (X) followed by Sharpless dihydroxylation.