Retracted: The Manganese(I)‐Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

Passera, Alessandro; Mezzetti, Antonio

doi:10.1002/ange.201912605

Angewandte Chemie

2019

DOI: 10.1002/ange.201912605

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Retracted: The Manganese(I)‐Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

Alessandro Passera

Antonio Mezzetti

Abstract: The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2‐propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.

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Cited by 8 publications

(1 citation statement)

References 89 publications

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“…Ru, Rh, and Ir are extremely scarce elements, occurring at very low abundances in the earth's crust (5 × 10 −5 -10 −4 ppm) 41 . Owing to the low abundance and high cost of the noble metals, the development of cheap earth-abundant metal substitutes to the noble metal catalysts is of high significance [42][43][44][45][46][47][48][49][50][51][52][53][54] .…”

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confidence: 99%

Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids

Xiao

Huang

et al. 2020

Nat Commun

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Asymmetric hydrogenation of α,β-unsaturated acids catalyzed by noble metals has been well established, whereas, the asymmetric hydrogenation with earth-abundant-metal was rarely reported. Here, we describe a cobalt-catalyzed asymmetric hydrogenation of α,β-unsaturated carboxylic acids. By using chiral cobalt catalyst bearing electron-donating diphosphine ligand, high activity (up to 1860 TON) and excellent enantioselectivity (up to >99% ee) are observed. Furthermore, the cobalt-catalyzed asymmetric hydrogenation is successfully applied to a broad spectrum of α,β-unsaturated carboxylic acids, such as various α-aryl and αalkyl cinnamic acid derivatives, α-oxy-functionalized α,β-unsaturated acids, α-substituted acrylic acids and heterocyclic α,β-unsaturated acids (30 examples). The synthetic utility of the protocol is highlighted by the synthesis of key intermediates for chiral drugs (6 cases). Preliminary mechanistic studies reveal that the carboxy group may be involved in the control of the reactivity and enantioselectivity through an interaction with the metal centre.

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confidence: 99%

Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids

Xiao

Huang

et al. 2020

Nat Commun

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Nickel‐Catalyzed Asymmetric Hydrogenation of 2‐Amidoacrylates

Chen

et al. 2020

Angewandte Chemie

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Earth‐abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2‐amidoacrylates, affording the chiral α‐amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α‐amino acids, β‐amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium‐labeling experiments and computational calculations.

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Manganese‐Catalyzed anti‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides

et al. 2020

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A Mn‐catalyzed diastereo‐ and enantioselective hydrogenation of α‐substituted β‐ketoamides has been realized for the first time under dynamic kinetic resolution conditions. anti‐α‐Substituted β‐hydroxy amides, which are useful building blocks for the synthesis of bioactive molecules and chiral drugs, were prepared in high yields with excellent selectivity (up to >99 % dr and >99 % ee) and unprecedentedly high activity (TON up to 10000). The origin of the excellent stereoselectivity was clarified by DFT calculations.

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Retracted: The Manganese(I)‐Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

Cited by 8 publications

References 89 publications

Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids

Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids

Nickel‐Catalyzed Asymmetric Hydrogenation of 2‐Amidoacrylates

Manganese‐Catalyzed anti‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides

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