4.7 Article

Asymmetric hydrogenation of α-hydroxy ketones with an iridium/f-amphox catalyst: efficient access to chiral 1,2-diols

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 4, Pages 555-559

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00810k

Keywords

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Funding

  1. Wuhan University [203273463, 203600400006]
  2. Important Sci-Tech Innovative Project of Hubei Province [2015ACA058]
  3. 111 Project of the Ministry of Education of China
  4. National Natural Science Foundation of China [21372179, 21432007, 21502145]

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We successfully applied tridentate f-amphox ligands to the iridium-catalytic asymmetric hydrogenation of various alpha-hydroxy ketones to afford the corresponding chiral 1,2-diols with excellent results (almost all products up to 99% yield and >99% ee). The resulting chiral 1,2-diols and their derivatives are important synthetic and pharmaceutical intermediates. Our catalytic system displayed extremely high activity, achieving up to 1 000 000 turnover number (TON). The great performance of this asymmetric hydrogenation makes the preparation of various chiral 1,2-diols highly practical with great potential.

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