Highly Enantioselective Rhodium-Catalyzed Hydrogenation of β-Dehydroamino Acid Derivatives Using Monodentate Phosphoramidites

Highly Enantioselective Rhodium-Catalyzed Hydrogenation of β-Dehydroamino Acid Derivatives Using Monodentate Phosphoramidites

New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-β-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic system...

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Veröffentlicht in:Journal of the American Chemical Society 2002-12, Vol.124 (49), p.14552-14553
Hauptverfasser: Peña, Diego, Minnaard, Adriaan J, de Vries, Johannes G, Feringa, Ben L
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemistry
Catalysis
Chemistry
Exact sciences and technology
Hydrogenation
Organic chemistry
Organophosphorus Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-β-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-β-(acylamino)acrylates (98−99% ee) and (Z)-β-(acylamino)acrylates (92−95% ee) based on phosphoramidites 2 and 3, respectively.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja028235t