Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction.


  • Many chiral phosphorus-based auxiliary ligands are available for transition metals in asymmetric, catalytic, homogeneous reductions of alkenes. Particularly noteworthy are the diphosphine ligands DTPAMP, developed by William S. Knowles (Nobel Prize, 2001), and BINAP, developed by Ryoji Noyori (Nobel Prize, 2001).
    BINAP is available as either the (+)- or (-)-enantiomer and displays broad utility in rhodium- and ruthenium-catalyzed asymmetric hydrogenations of β-keto esters and alkenes.
    • George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 5 : Functional Group Transformations: The Chemistry of Carbon-Carbon π-Bonds and Related Reactions

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