Synthesis of substituted pyrrolin-4-ones from amino acids in mild conditions via a gold-catalyzed approach.
The gold-catalyzed cyclization of various alpha-amino-ynone derivatives gave the corresponding pyrrolin-4-ones in high yields. Moreover, the use of gold(III) oxide as catalyst allows a moderate to total stereocontrol during the cyclization. These pyrrolin-4-ones are highly useful intermediates for the synthesis of functionalized pyrrolidines and other natural products.
Gouault
Nicolas
N
EA Substances Lichéniques et Photoprotection, Université de Rennes1, 2 avenue du Pr. Léon Bernard, 35043 Rennes Cedex, France. nicolas.gouault@univ-rennes1.fr
Le Roch
Myriam
M
Cornée
Carole
C
David
Michèle
M
Uriac
Philippe
P
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D011758:Pyrroles; C013231:pyrroline; D006046:Gold