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Base-Free Asymmetric Transfer Hydrogenation of 1,2-Di- and Monoketones Catalyzed by a (NH)2P2-Macrocyclic Iron(II) Hydride

Authors

M. Sc. Lorena De Luca,

Close author notesDepartement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Zürich, Switzerland

Prof. Dr. Antonio Mezzetti

Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Zürich, Switzerland

First published: 18 August 2017

Full publication historyDOI: 10.1002/anie.201706261 View/save citationCited by (CrossRef): 0 articles Check for updates Citation tools

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Abstract

The hydride isonitrile complex [FeH(CNCEt3)(1 a)]BF4 (2) containing a chiral P2(NH)2 macrocycle (1 a), in the presence of 2-propanol as hydrogen donor, catalyzes the base-free asymmetric transfer hydrogenation (ATH) of prostereogenic ketones to alcohols and the hemihydrogenation of benzils to benzoins, which contain a base-labile stereocenter. Benzoins are formed in up to 83 % isolated yield with enantioselectivity reaching 95 % ee. Ketones give the same enantioselectivity observed with the parent catalytic system [Fe(CNCEt3)2(1 a)] (3 a) that operates with added NaOtBu.