Iodocyclization of chiral CF3-allylmorpholinones: a versatile strategy for the synthesis of enantiopure alpha-Tfm-prolines and alpha-Tfm-dihydroxyprolines.
An efficient iodocyclization reaction of a chiral Tfm-allylmorpholinone provides a straightforward route to alpha-Tfm-prolines and alpha-Tfm-dihydroxyprolines. The methodologies developed are particularly well adapted for gram-scale synthesis of enantiopure compounds.
Caupène
Caroline
C
Laboratoire Synthèse Organique Sélective et Chimie Organométallique, Université de Cergy-Pontoise, UMR CNRS 8123, F-95000 Cergy-Pontoise, France.
Chaume
Grégory
G
Ricard
Louis
L
Brigaud
Thierry
T
D018360:Crystallography, X-Ray; D003500:Cyclization; D005466:Fluorocarbons / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009025:Morpholines / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005466:Fluorocarbons; D009025:Morpholines; D011392:Proline