Endo-benzonorbornen-2-ol as an efficient non-natural chiral auxiliary in the asymmetric aza-Diels–Alder reactions between cyclopentadiene and (1-phenylethyl)iminoacetates

• Published in: RSC advances Vol. 4; no. 101; pp. 57768 - 57772
• Main Authors: Sousa, Carlos A. D., Maestro, Miguel A., Garcia-Mera, Xerardo, Rodríguez-Borges, José E.
• Format: Journal Article
• Language: English
• Published: 01.01.2014
• Subjects: Adducts; Asymmetry; Chromatography; Cycloaddition; Cyclopentadiene; Optical properties; Optical rotation; X-rays

Exo-2-azabicyclo[2.2.1]hept-5-enes were obtained by cycloaddition reactions between cyclopentadiene and protonated (S)- and (R)-1-phenylethylimines of (1R,endo)-benzonorbornen-2-yl glyoxylate. The non-natural (1R,endo)-benzonorbornen-2-ol proved to be an efficient chiral auxiliary in these asymmetri...