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Enantioselective synthesis of 2-oxazolidinones by ruthenium(II)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

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Abstract

An efficient synthesis of optically active 4-substituted 2-oxazolidinones by the ruthenium(II)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones was developed. Excellent enantioselectivities (up to 96% ee) and yields (up to 99%) were obtained for a variety of substrates, bearing a range of functional groups and useful motifs. The hydrogenation reaction was successfully scaled up to gram scale using low catalyst loading. Moreover, the utility of this methodology was demonstrated by the transformation of the enantioenriched product into the corresponding chiral β-amino alcohol, a bisoxazoline ligand, and the formal synthesis of (−)-aurantioclavine.

Graphical abstract: Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

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Publication details

The article was received on 24 Apr 2018, accepted on 28 Jun 2018 and first published on 28 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC01869C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Enantioselective synthesis of 2-oxazolidinones by ruthenium(II)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

    W. Li, M. Wollenburg and F. Glorius, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC01869C

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