Enantioselective synthesis of α-heteroarylpyrrolidines by copper-catalyzed 1,3-dipolar cycloaddition of α-silylimines.
α-Heteroarylpyrrolidines have been efficiently prepared via 1,3-dipolar cycloaddition between silylimines and activated olefins. In the presence of Cu(CH3CN)4PF6/Walphos as catalytic system, high levels of enantioselectivity (up to ≥99% ee) and diastereoselectivity were achieved (major formation of C-2/C-4 trans-substituted pyrrolidines). The reaction is compatible with a broad variety of dipolarophiles including maleimides, maleates, fumarates, nitroalkenes, and vinylsulfones. The resulting cycloadducts can be transformed into bioactive pyrrolidine derivatives.
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , Cantoblanco, 28049 Madrid, Spain.
Ana
A
Pascual-Escudero
María
M
González-Esguevillas
Silvia
S
Padilla
Javier
J
Adrio
Juan C
JC
Carretero
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry*; D008298:Maleates / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D007097:Imines; D008298:Maleates; D009574:Nitro Compounds; D011759:Pyrrolidines; D012821:Silanes; D003300:Copper