Enantioselective Syntheses of 2-Azabicyclo[2.2.1]heptanes via Brønsted Acid Catalyzed Ring-Opening of <i>meso</i>-Epoxides
Min Cai, Jiao Ma, Qimin Wu, Aijun Lin, Hequan Yao
Abstract
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.
Topics & Concepts
ChemistryPhosphoric acidRing (chemistry)CatalysisEnantioselective synthesisAmideDerivatizationOrganic chemistryCombinatorial chemistryHigh-performance liquid chromatographyAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods