Diastereoselective synthesis of hexahydro-3H-pyrrolyzin-3-ones through Pd-catalyzed carboamination.
The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd(2)(dba)(3), Xphos, and Cs(2)CO(3) in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.
Bagnoli
Luana
L
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy.
Cacchi
Sandro
S
Fabrizi
Giancarlo
G
Goggiamani
Antonella
A
Scarponi
Catalina
C
Tiecco
Marcello
M
D000586:Amination; D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011759:Pyrrolidines; D011760:Pyrrolidinones; D010165:Palladium