Rapid asymmetric synthesis of highly functionalized C5 chiral synthons. Practical preparation of trans-3 -hydroxy-D-proline
A stereocontrolled synthesis of (2R, 3R)-3-hydroxyproline 5 has been achieved in 33% overall yield from a prochiral β-ketoester : the methyl 5,5-dimethoxy-3-oxopentanoate 6. The key intermediate is the richly functionalized compound 4 which presented three different oxygenated groups and an anti relationship between the alcohol and the amine.