Hydrogen-bond-mediated enantio- and regioselectivity in a Ru-catalyzed epoxidation reaction.
A chiral epoxidation catalyst based on a tricyclic octahydro-1H-4,7-methanoisoindol-1-one scaffold, in which a hydrogen bonding site and the catalytically active ruthenium center are spatially separated, was synthesized. It was shown that epoxidation reactions in such a supramolecular catalyst occur with high enantio- and regioselectivity because the hydrogen bonds expose the substrate to the ruthenium porphyrin complex with a clear conformational preference. The epoxidation of 3-vinylquinolone proceeded in up to 95% ee (71% yield).
Fackler
Philipp
P
Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.
Berthold
Carola
C
Voss
Felix
F
Bach
Thorsten
T
D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D012428:Ruthenium / Q000737:chemistry*
D004852:Epoxy Compounds; D012428:Ruthenium