ChemInform Abstract: The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. Part 1. The Polyhydroxylated Pyrrolidines.

✍ Scribed by Y. HUANG; D. R. DALTON; P. J. CARROLL

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199722227

✦ Synopsis

The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. Part 1. The Polyhydroxylated Pyrrolidines.

-All eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines, e. g. (IX) and (X), are prepared from L-serine methylester (I) or D-serine methylester, respectively. Key step in the synthesis of these compounds, which are potential glycosidase inhibitors, is the stereoselective dihydroxylation of propenoates, e.g. (V), which is investigated in detail. -(HUANG, Y.;