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Issue 4, 2008
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BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?

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Abstract

In discovering the remarkable catalytic properties of BINOL-derived phosphoramidites (binoP–NR2), Dutch researchers recently achieved a long-awaited breakthrough in asymmetric catalysis. For the first time, easily accessible monodentate chiral P(III) ligands turned out to provide high enantioselectivities when used in rhodium-catalysed olefin hydrogenation. The simplest ligand representative of this family is MonoPhos™, which can be made straightforwardly from BINOL and hexamethylphosphorous triamide. Since the first publication dealing with such catalysts (J. Am. Chem. Soc., 2000), a variety of binoP–NRR′ ligands have been reported in which the amino group bears a functional substituent or a stereogenic centre. This critical review examines the impact of the presence of such a functionality in the amino group on catalytic olefin hydrogenation reactions.

Graphical abstract: BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?

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Publication details

The article was received on 14 Jan 2008 and first published on 18 Feb 2008


Article type: Critical Review
DOI: 10.1039/B714519E
Citation: Chem. Soc. Rev., 2008,37, 839-864
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    BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?

    L. Eberhardt, D. Armspach, J. Harrowfield and D. Matt, Chem. Soc. Rev., 2008, 37, 839
    DOI: 10.1039/B714519E

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