Product Name
NO-Feng-PPhPPr, L-PrPh, 95%
Molecular Formula
C25H32N4O4
Certificate of Analysis (COA)
IUPAC Name
(1R,2S)-1-oxido-1-3-(1R,2S)-1-oxido-2-(phenylcarbamoyl)pyrrolidin-1-ium-1-ylpropyl-N-phenylpyrrolidin-1-ium-2-carboxamide
InChI Key
FMBOOIXMUVEDMO-BYSIJJKSSA-N
SMILES
C1CC@H(N@@+(C1)(CCCN@@+2(CCCC@H2C(=O)NC3=CC=CC=C3)O-)O-)C(=O)NC4=CC=CC=C4
What is NO-Feng-PPhPPr used for?
NO-Feng-PPhPPr is primarily used as a chiral N,N'-dioxide ligand for asymmetric catalysis and enantioselective synthesis. It is widely applied in the construction of chiral Lewis acid catalyst systems for stereoselective organic transformations.
What is the alternative name of NO-Feng-PPhPPr?
NO-Feng-PPhPPr is commonly referred to as L-PrPh, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PPhPPr?
It belongs to the Feng Chiral N,N'-Dioxide Ligand Series, a class of privileged ligands known for strong metal coordination ability and excellent stereochemical control.
Which catalytic reactions can benefit from this ligand?
NO-Feng-PPhPPr has been used in a variety of asymmetric transformations, including:
- Asymmetric Michael reactions
- Mannich reactions
- Aldol reactions
- Cycloaddition reactions
- Hetero-Diels–Alder reactions
- Lewis acid catalysis
- Enantioselective carbon–carbon bond formation
These reactions benefit from the well-defined chiral environment provided by the ligand–metal complex.
Which metal catalysts are commonly used with NO-Feng-PPhPPr?
The ligand can coordinate with multiple Lewis acidic metals, such as:
- Sc(III)
- Cu(II)
- Fe(II/III)
- Mg(II)
- Ni(II)
- Yb(III)
- Other rare-earth metal catalysts
Can NO-Feng-PPhPPr be used for pharmaceutical synthesis research?
Yes. It is widely used in the synthesis of enantioenriched pharmaceutical intermediates, natural products, and biologically active molecules.
Why are Feng ligands important in asymmetric catalysis?
Feng ligands combine rigidity and flexibility in one framework, enabling precise control of substrate orientation and transition-state organization, leading to high enantioselectivity.
What are the advantages of NO-Feng-PPhPPr compared with conventional ligands?
- High enantioselectivity
- Strong metal coordination ability
- Broad substrate compatibility
- Excellent catalytic efficiency
- Tunable steric and electronic properties
- Wide application in asymmetric catalysis
What makes L-PrPh different from other Feng ligands?
L-PrPh contains a phenyl-substituted aromatic framework, which adjusts steric hindrance and electronic effects around the catalytic center, influencing selectivity and substrate scope.
Can NO-Feng-PPhPPr be used in Lewis acid catalysis?
Yes. It is designed to form highly active chiral Lewis acid complexes with various metal ions and is widely used in asymmetric catalysis.
How should NO-Feng-PPhPPr be stored?
It should be stored in a dry, sealed container, protected from light and moisture. Long-term storage at −20°C is recommended.
Does catalytic performance depend on reaction conditions?
Yes. Key factors such as metal source, solvent, temperature, catalyst loading, and substrate structure significantly affect catalytic activity and enantioselectivity.