title: Asymmetric Diels-Alder, Michael, and aldol reactions using a planar chiral 1,3-oxazol-2(3H)-one derived from (R)-(+)-4-hydroxy-[2.2]paracyclophane.
abstract: (+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of alpha,beta-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face-diastereoselectivity is good and is controlled by the spatial relationship between the prochiral center and the C9-C10 ethylene bridge of the [2.2]paracyclophane moiety. The chiral auxiliary is easily removed and quantitatively recovered.
authors.affiliation: Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8-06123 Perugia, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Cipiciani
authors.forename: Francesco
authors.initials: F
authors.lastname: Fringuelli
authors.forename: Oriana
authors.initials: O
authors.lastname: Piermatti
authors.forename: Ferdinando
authors.initials: F
authors.lastname: Pizzo
authors.forename: Renzo
authors.initials: R
authors.lastname: Ruzziconi