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Issue 11, 2018
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Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

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Abstract

Herein, we report a Zn–ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, the enantioenriched hydrazine products can be readily converted into versatile building blocks such as α-amino carbonyl compounds and β-amino alcohols.

Graphical abstract: Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

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Publication details

The article was received on 10 Jan 2018, accepted on 13 Feb 2018 and first published on 14 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00147B
Citation: Chem. Sci., 2018,9, 2975-2980
  • Open access: Creative Commons BY license
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    Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

    B. M. Trost, J. S. Tracy and T. Saget, Chem. Sci., 2018, 9, 2975
    DOI: 10.1039/C8SC00147B

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