What question did this study set out to answer?

Determine whether pairing chiral phosphoramidite ligands with achiral monodentate ligands improves the catalytic rate and enantioselectivity during rhodium-catalyzed asymmetric hydrogenation.

June 1, 2005Angewandte Chemie International EditionOpen Access

Achiral Ligands Dramatically Enhance Rate and Enantioselectivity in the Rh/Phosphoramidite‐Catalyzed Hydrogenation of α,β‐Disubstituted Unsaturated Acids

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Authors

RHRob HoenUniversitat de Barcelona JBJeroen A. F. BoogersDSM (Netherlands)HBHeiko BernsmannStanford University

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Implication

Experimental investigation demonstrates improved enantioselectivity in rhodium-catalyzed hydrogenation via mixed-ligand complexes, indicating a potent strategy for asymmetric synthesis.

Key Points

Determine whether pairing chiral phosphoramidite ligands with achiral monodentate ligands improves the catalytic rate and enantioselectivity during rhodium-catalyzed asymmetric hydrogenation.
Formulated a mixed-ligand catalytic system combining a chiral phosphoramidite ligand and an achiral monodentate ligand with a rhodium precursor.
Evaluated catalytic performance and enantiomeric excess in the asymmetric hydrogenation of α,β-disubstituted unsaturated acids (cinnamic acid derivatives).
The heterocombination of chiral and achiral monodentate ligands provided a dramatic increase in reaction rate relative to the corresponding homocomplexes.
Mixed-ligand rhodium catalysts delivered enantioselectivity up to 99%, substantially outperforming both homocomplex benchmarks.

Cite This Study

Hoen et al. (2005) studied this question.

synapsesocial.com/papers/6a931a39cbe169eedcf8bf85 https://doi.org/10.1002/anie.200500784

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Implication

Experimental investigation demonstrates improved enantioselectivity in rhodium-catalyzed hydrogenation via mixed-ligand complexes, indicating a potent strategy for asymmetric synthesis.

Achiral Ligands Dramatically Enhance Rate and Enantioselectivity in the Rh/Phosphoramidite‐Catalyzed Hydrogenation of α,β‐Disubstituted Unsaturated Acids

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Implication

Key Points

Cite This Study

Achiral Ligands Dramatically Enhance Rate and Enantioselectivity in the Rh/Phosphoramidite‐Catalyzed Hydrogenation of α,β‐Disubstituted Unsaturated Acids

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Key Points

Cite This Study

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