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

Xiaoyong Du, Ye Xiao, Jia-Ming Huang, Yao Zhang, Ya-Nan Duan, Heng Wang, Chuan Shi, Gen-Qiang Chen () and Xumu Zhang ()
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Xiaoyong Du: Southern University of Science and Technology
Ye Xiao: Southern University of Science and Technology
Jia-Ming Huang: Southern University of Science and Technology
Yao Zhang: Southern University of Science and Technology
Ya-Nan Duan: Southern University of Science and Technology
Heng Wang: Southern University of Science and Technology
Chuan Shi: Southern University of Science and Technology
Gen-Qiang Chen: Southern University of Science and Technology
Xumu Zhang: Southern University of Science and Technology

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract 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 α-alkyl 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.

Date: 2020
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DOI: 10.1038/s41467-020-17057-z

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