Application of a new amidophosphite ligand to Rh-catalyzed asymmetric hydrogenation of β-dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co-solvents

New chiral amidophosphite ligand was synthesized and tested in the Rh‐catalyzed asymmetric hydrogenation of (Z)‐β‐(acylamino)acrylates in protic solvents and supercritical carbon dioxide (scCO2) The catalytic performance is affected greatly by the acidity of the solvents. Better enantioselectivity (...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2011-09, Vol.23 (8), p.624-627
Main Authors: Lyubimov, Sergey E., Rastorguev, Eugenie A., Davankov, Vadim A.
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
asymmetric hydrogenation
Carbon Dioxide - chemistry
Catalysis
co-solvents
Hydrogenation
Ligands
Molecular Structure
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
phosphoramidite ligand
Rhodium - chemistry
Solvents - chemistry
Stereoisomerism
supercritical carbon dioxide
β-amino acids
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Summary:New chiral amidophosphite ligand was synthesized and tested in the Rh‐catalyzed asymmetric hydrogenation of (Z)‐β‐(acylamino)acrylates in protic solvents and supercritical carbon dioxide (scCO2) The catalytic performance is affected greatly by the acidity of the solvents. Better enantioselectivity (up to 88% ee) was achieved in scCO2 containing 1,1,1,3,3,3‐hexafluoro‐2‐propanol, compared to neat protic solvents. Chirality, 2011. © 2011 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20992