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Frontispiece: Iron/Brønsted Acid Catalyzed Asymmetric Hydrogenation: Mechanism and Selectivity‐Determining Interactions
Author(s) -
Hopmann Kathrin H.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201582862
Subject(s) - selectivity , asymmetric hydrogenation , transfer hydrogenation , imine , catalysis , phosphoric acid , chemistry , hydride , substrate (aquarium) , brønsted–lowry acid–base theory , noyori asymmetric hydrogenation , hydrogen bond , combinatorial chemistry , hydrogen , enantioselective synthesis , stereochemistry , organic chemistry , molecule , ruthenium , oceanography , geology
Asymmetric Hydrogenation The asymmetric hydrogenation of imines with Knölker's iron complex in the presence of chiral phosphoric acids was investigated computationally at the DFT‐D level in the Full Paper by K. H. Hopmann on page 10020 ff. At the selectivity‐determining step, hydrogen bonding to the acid facilitates positioning of the imine and the iron complex for hydride transfer. Due to the large 9‐anthracenyl substituents, the acid appears to embrace the achiral complex and substrate, providing a chiral environment, which through noncovalent interactions (such as CH–π and CH⋅⋅⋅O) mediates the asymmetric hydrogenation. (Photograph of the hands by T. Zbrodko/Shutterstock.)