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A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides

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Abstract

Nickel-catalyzed asymmetric hydrogenation of challenging tetrasubstituted fluorinated enamides has been achieved, affording chiral α-fluoro-β-amino esters in high yields with excellent diastereo- and enantioselectivities (up to 98% yield, >99 : 1 dr, up to >99% ee). Deuterium-labeling experiments and control experiments were conducted to probe the mechanism, and the results indicated that the acidity of the solvent plays a critical role in the control of diastereoselectivity by trapping the adduct of nickel hydride to C[double bond, length as m-dash]C bonds via protonolysis, giving the hydrogenation product with stereospecific syn-selectivity. This protocol provides efficient access to chiral α-fluoro-β-amino esters which have important potential applications in organic synthesis and medicinal chemistry.

Graphical abstract: A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides

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Publication details

The article was received on 09 Sep 2018, accepted on 03 Oct 2018 and first published on 16 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC04002H
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides

    Y. Guan, Z. Han, X. Li, C. You, X. Tan, H. Lv and X. Zhang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04002H

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