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Iron(II)‐Catalyzed Asymmetric Hydrosilylation of Acetophenone
Author(s) -
Flückiger Michelle,
Togni Antonio
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100550
Subject(s) - hydrosilylation , chemistry , acetophenone , enantioselective synthesis , catalysis , stereocenter , phenylsilane , cyclopentadiene , ligand (biochemistry) , organic chemistry , medicinal chemistry , stereochemistry , polymer chemistry , combinatorial chemistry , biochemistry , receptor
Four new ligands containing a pentasubstituted cyclopentadiene tethered to a stereogenic diamine unit have been prepared and used in the iron‐catalyzed enantioselective hydrosilylation of acetophenone. Catalytically active species have been generated in situ starting from various sources of iron. Fe(acac) 2 was the catalyst precursor of choice, whereas other simple Fe II or Fe III compounds resulted in significantly lower or no catalytic activity. Quantitative conversions were obtained working with 4 mol‐% Fe at room temp. and phenylsilane as the reducing agent. Under these conditions, ligand 4 afforded an enantioselectivity of 37 % ee . Attempts to isolate the single‐component Fe complexes containing ligands 3 – 6 have failed so far.