A memory of chirality approach to the stereoselective synthesis of 4-hydroxy-alpha-methylprolines.
To extend the memory of chirality (MOC) methodology to structurally more diverse compounds, the synthesis of 4-hydroxy-alpha-methylprolines was undertaken. Yield and selectivity were very good, with an unexpected reversal in selectivity observed for the cyclization of one adduct with an unprotected hydroxyl.
Kolaczkowski
Lawrence
L
Abbott Global Pharmaceutical Research and Development, Process Chemistry, 1401 Sheridan Road, North Chicago, Illinois 60064-6285, USA. larry.kolaczkowski@abbott.com
Barnes
David M
DM
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011392:Proline