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Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
Author(s) -
Rodriguez Sandra,
Uria Uxue,
Reyes Efraim,
Carrillo Luisa,
Tejero Tomás,
Merino Pedro,
Vicario Jose L.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000650
Subject(s) - desymmetrization , enantioselective synthesis , phosphoric acid , catalysis , chemistry , organocatalysis , octane , stereoselectivity , organic chemistry , ring (chemistry) , stereochemistry , combinatorial chemistry
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.