Base-free Asymmetric Transfer Hydrogenation of 1,2-Di- and Monoketones Catalyzed by a Chiral Iron(II) Hydride

Open access
Date
2018-04Type
- Journal Article
Abstract
The chiral iron(II) hydride complex [FeH(CNCEt3)(1a)](BF4) (3, 1a is a chiral macrocycle with an (NH)2P2 donor set) catalyzes the base-free transfer hydrogenation (ATH) of prochiral ketones and the hemireduction of benzils to the corresponding benzoins using i PrOH as hydrogen donor. Ketones give the same excellent enantio-selectivity (up to 99% ee) as the parent catalyst [Fe(CNCEt3)2(1a)](BF4)2 (2), which is only active upon treatment with NaOtBu. Benzoins, whose labile stereocenter is known to undergo racemization under basic conditions, are formed in up to 83% isolated yield with enantioselectivity as high as 95%. Show more
Permanent link
https://doi.org/10.3929/ethz-b-000276421Publication status
publishedExternal links
Journal / series
ChimiaVolume
Pages / Article No.
Publisher
Swiss Chemical SocietySubject
Asymmetric transfer hydrogenation; Base-free; Benzoin; Hydride complexes; Iron catalysisOrganisational unit
08812 - Mezzetti, Antonio (Tit-Prof.) (ehemalig) / Mezzetti, Antonio (Tit.-Prof.) (former)
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