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

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Yu-Qing Guan
  • Zhengyu Han
  • Xiuxiu Li
  • Cai You
  • Hui Lv
  • Xumu Zhang

Detail(s)

Original languageEnglish
Pages (from-to)252-256
Journal / PublicationChemical Science
Volume10
Issue number1
Online published16 Oct 2018
Publication statusPublished - 7 Jan 2019
Externally publishedYes

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═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. © The Royal Society of Chemistry 2019.

Citation Format(s)

A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides. / Guan, Yu-Qing; Han, Zhengyu; Li, Xiuxiu et al.
In: Chemical Science, Vol. 10, No. 1, 07.01.2019, p. 252-256.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review