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Issue 3, 2017
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Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

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Abstract

We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.

Graphical abstract: Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

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Publication details

The article was received on 22 Aug 2016, accepted on 14 Nov 2016 and first published on 15 Nov 2016


Article type: Edge Article
DOI: 10.1039/C6SC03764J
Citation: Chem. Sci., 2017,8, 1977-1980
  • Open access: Creative Commons BY license
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    Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

    S. Yang, W. Che, H. Wu, S. Zhu and Q. Zhou, Chem. Sci., 2017, 8, 1977
    DOI: 10.1039/C6SC03764J

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