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Diastereo- and Enantioselective anti-Selective Hydrogenation of α-Amino-β-keto Ester Hydrochlorides and Related Compounds Using Transition-Metal-Chiral-Bisphosphine Catalysts.
- Source :
- Chemical Record; Apr2014, Vol. 14 Issue 2, p235-250, 16p
- Publication Year :
- 2014
-
Abstract
- This review describes our recent works on the diastereo- and enantioselective synthesis of anti-β-hydroxy-α-amino acid esters using transition-metal-chiral-bisphosphine catalysts. A variety of transition metals, namely ruthenium ( Ru), rhodium ( Rh), iridium ( Ir), and nickel ( Ni), in combination with chiral bisphosphines, worked well as catalysts for the direct anti-selective asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides, yielding anti-β-hydroxy-α-amino acid esters via dynamic kinetic resolution ( DKR) in excellent yields and diastereo- and enantioselectivities. The Ru-catalyzed asymmetric hydrogenation of α-amino-β-ketoesters via DKR is the first example of generating anti-β-hydroxy-α-amino acids. Complexes of iridium and axially chiral bisphosphines catalyze an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides via dynamic kinetic resolution. A homogeneous Ni-chiral-bisphosphine complex also catalyzes an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides in an anti-selective manner. As a related process, the asymmetric hydrogenation of the configurationally stable substituted α-aminoketones using a Ni catalyst via DKR is also described. [ABSTRACT FROM AUTHOR]
- Subjects :
- TRANSITION metals
RUTHENIUM
RHODIUM
KINETIC resolution
HYDROGENATION
Subjects
Details
- Language :
- English
- ISSN :
- 15278999
- Volume :
- 14
- Issue :
- 2
- Database :
- Complementary Index
- Journal :
- Chemical Record
- Publication Type :
- Academic Journal
- Accession number :
- 95516563
- Full Text :
- https://doi.org/10.1002/tcr.201300032