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

Antonio Cipiciani; Francesco Fringuelli; Oriana Piermatti; Ferdinando Pizzo; Renzo Ruzziconi

doi:10.1021/jo016383g

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

J Org Chem. 2002 Apr 19;67(8):2665-70. doi: 10.1021/jo016383g.

Authors

Antonio Cipiciani¹, Francesco Fringuelli, Oriana Piermatti, Ferdinando Pizzo, Renzo Ruzziconi

Affiliation

¹ Dipartimento di Chimica, Università di Perugia, via Elce di Sotto, 8-06123 Perugia, Italy.

PMID: 11950314
DOI: 10.1021/jo016383g

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.