Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
Fecha
2020-02-10Autor
Rodríguez López, Sandra
Reyes Martín, Efraim
Tejero, Tomás
Merino, Pedro
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Angewandte Chemie Int. Ed. 59(17) : 6780-6784(2020)
Resumen
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.