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Chiral (Cyclopentadienone)iron Complexes for the Catalytic Asymmetric Hydrogenation of Ketones
Author(s) -
Gajewski Piotr,
RenomCarrasco Marc,
Facchini Sofia Vailati,
Pignataro Luca,
Lefort Laurent,
de Vries Johannes G.,
Ferraccioli Raffaella,
Forni Alessandra,
Piarulli Umberto,
Gennari Cesare
Publication year - 2015
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.201500146
Subject(s) - chemistry , enantioselective synthesis , moiety , catalysis , asymmetric hydrogenation , stereochemistry , chirality (physics) , medicinal chemistry , organic chemistry , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
Three chiral (cyclopentadienone)iron complexes derived from ( R )‐BINOL ( CK1 – 3 ) were synthesized and their structures unambiguously confirmed by X‐ray analysis ( CK3 ). Under suitable conditions for the in situ conversion into the corresponding (hydroxycyclopentadienyl)iron hydrides (Me 3 NO, H 2 ), the new chiral complexes were tested in the catalytic asymmetric hydrogenation of ketones, showing moderate to good enantioselectivity. In particular, the complex bearing methoxy substituents at the 3,3′‐positions of the binaphthyl moiety ( CK2 ) proved remarkably more enantioselective than the unsubstituted one ( CK1 ) and reached the highest level of enantioselectivity (up to 77 % ee ) ever obtained with chiral (cyclopentadienone)iron complexes.