Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
Sandra Rodríguez, Uxue Uria, Efraím Reyes, Luisa Carrillo, Tomás Tejero, Pedro Merino, José L. Vicário
Abstract
The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the desymmetrization of the starting material and leads to the direct formation of the 8-azabicyclo[3.2.1]octane scaffold with excellent stereoselectivity. The synthetic applicability of the reaction was demonstrated by the enantioselective synthesis of the two natural products (-)-α-tropanol and (+)-ferruginine.
Topics & Concepts
DesymmetrizationEnantioselective synthesisChemistryPhosphoric acidCatalysisOrganocatalysisOctaneStereoselectivityOrganic chemistryRing (chemistry)StereochemistryCombinatorial chemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsTraditional and Medicinal Uses of Annonaceae