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

• Published in: Journal of organic chemistry Vol. 67; no. 8; pp. 2665 - 2670
• Main Authors: Cipiciani, Antonio, Fringuelli, Francesco, Piermatti, Oriana, Pizzo, Ferdinando, Ruzziconi, Renzo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.04.2002; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; N-ACYLOXAZOLIDINONES; ENANTIOSELECTIVE SYNTHESIS; ONE-POT SYNTHESIS; STAUDINGER REACTION; ALLYLIC ALCOHOLS; KINETIC RESOLUTION; MONOPEROXYPHTHALIC ACID; OXAZOLIDINONE AUXILIARY; BETA-HYDROXY ACIDS; CARBOXYLIC-ACIDS; Michael addition; Diels Alder addition; Diastereoselectivity; Aldol condensation; Planar molecule; Unsaturated compound; Imide; Chiral auxiliary; Cyclization; Asymmetric reaction; Cyclophane; Chemical synthesis; Enolate; Oxazole derivatives; Oxygen nitrogen heterocycle
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo016383g

(+)-(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 α,β-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.