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

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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%.

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Keywords: ASYMMETRIC TRANSFER HYDROGENATION; BASE-FREE; BENZOIN; HYDRIDE COMPLEXES; IRON CATALYSIS

Document Type: Research Article

Affiliations: 1: Department of Chemistry and Applied Biosciences, ETH Zurich, CH-8093 Zurich, Switzerland. [email protected] 2: Department of Chemistry and Applied Biosciences, ETH Zurich, CH-8093 Zurich, Switzerland

Publication date: April 1, 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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