Enantioselective Syntheses of 2-Azabicyclo[2.2.1]heptanes via Brønsted Acid Catalyzed Ring-Opening of meso -Epoxides.

A chiral phosphoric acid-catalyzed ring-opening of meso -epoxides was developed. A range of 2-azabicyclo[2.2.1]heptanes were obtained in high yields with excellent enantioselectivities. In addition, the hydroxyl and amide groups in the products provided handles for further derivatization.