Gold-catalyzed intramolecular hydroamination of o-alkynylbenzyl carbamates: a route to chiral fluorinated isoindoline and isoquinoline derivatives.
Enantiomerically pure fluorinated isoindoline and dihydroisoquinoline scaffolds have been prepared through a diastereoselective addition of fluorinated nucleophiles to Ellman's N-(tert-butanesulfinyl)imines followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate. A more favored 5-exo-dig mechanism was observed mainly due to an electronic effect of the fluorinated group.
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Santos
S
Fustero
Ignacio
I
Ibáñez
Pablo
P
Barrio
Miguel A
MA
Maestro
Silvia
S
Catalán
D000588:Amines / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D002219:Carbamates; D006845:Hydrocarbons, Fluorinated; D054833:Isoindoles; D007546:Isoquinolines; D006046:Gold