Polyfunctionalized pyrrolidines by Ugi multicomponent reaction followed by palladium-mediated SN2' cyclizations.
A 4-component Ugi reaction with a suitable isocyanide, followed by a novel secondary transformation involving a Pd(II)-mediated (R5 = H) or a Pd(0)-mediated (R5 = CO2Me) SN2' cyclization to give highly functionalized N-acyl-2-vinylpyrrolidines, is reported. The overall yields are usually good and in most cases the Pd(0)-catalyzed reaction gave the final product in almost quantitative yield.
Banfi
Luca
L
Università di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146-Genova, Italy.
Basso
Andrea
A
Cerulli
Valentina
V
Guanti
Giuseppe
G
Riva
Renata
R
D003500:Cyclization; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D011759:Pyrrolidines; D010165:Palladium