title: An amine-catalyzed enantioselective [3+2] cycloaddition of azomethine ylides and α,β-unsaturated aldehydes: applications and mechanistic implications.
abstract: The catalytic enantioselective [3+2] cycloaddition between azomethine ylides and α,β-unsaturated aldehydes catalyzed by α,α-diphenylprolinol has been studied in detail. In particular, the reaction has been extended to the use of 2-alkenylidene aminomalonates generated in situ as azomethine ylide precursors. These reactions lead to the formation of pyrrolidines containing a 5-alkenyl side chain with potential for chemical manipulation. Moreover, a detailed and concise computational study has been carried out to understand the exact nature of the mechanism of this reaction and especially the consequences derived from the incorporation of the chiral secondary amine catalyst on the reaction pathway.
authors.affiliation: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, PO Box 644, 48080 Bilbao, Spain.
authors.forename: Silvia
authors.initials: S
authors.lastname: Reboredo
authors.forename: Efraím
authors.initials: E
authors.lastname: Reyes
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
authors.forename: Dolores
authors.initials: D
authors.lastname: Badía
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo
authors.forename: Abel
authors.initials: A
authors.lastname: de Cózar
authors.forename: Fernando P
authors.initials: FP
authors.lastname: Cossío