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  • Title: Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization.
    Author: Rodriguez S, Uria U, Reyes E, Carrillo L, Tejero T, Merino P, Vicario JL.
    Journal: Angew Chem Int Ed Engl; 2020 Apr 20; 59(17):6780-6784. PubMed ID: 32039546.
    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.
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