Product Name
NO-Feng-PDPhMPPr, L-PrCPh2, 95%
Molecular Formula
C39H44N4O4
Certificate of Analysis (COA)
IUPAC Name
(2S)-N-benzhydryl-1-3-(2S)-2-(benzhydrylcarbamoyl)-1-oxidopyrrolidin-1-ium-1-ylpropyl-1-oxidopyrrolidin-1-ium-2-carboxamide
InChI Key
FPZGQUMTRJNZDE-WOBHDDJSSA-N
SMILES
C1CC@H(N+(C1)(CCCN+2(CCCC@H2C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)O-)O-)C(=O)NC(C5=CC=CC=C5)C6=CC=CC=C6
What is NO-Feng-PDPhMPPr used for?
NO-Feng-PDPhMPPr is primarily used as a chiral N,N'-dioxide ligand in asymmetric catalysis. It is widely applied in the formation of chiral Lewis acid complexes for stereoselective organic synthesis.
What is the alternative name of NO-Feng-PDPhMPPr?
NO-Feng-PDPhMPPr is commonly referred to as L-PrCPh₂, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PDPhMPPr?
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-PDPhMPPr can be used in a wide range 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-PDPhMPPr?
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
These complexes are widely used in asymmetric synthesis and catalyst development.
Can NO-Feng-PDPhMPPr be used for pharmaceutical synthesis research?
Yes. Chiral N,N'-dioxide ligands are 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 in the catalytic center. This leads to high enantioselectivity and broad reaction applicability.
What are the advantages of NO-Feng-PDPhMPPr compared with conventional ligands?
- High enantioselectivity
- Strong metal coordination ability
- Broad substrate compatibility
- Excellent catalytic efficiency
- Tunable steric/electronic properties
- Wide application in asymmetric transformations
What makes L-PrCPh₂ different from other Feng ligands?
L-PrCPh₂ contains a diphenylmethyl-substituted structural motif, providing a bulkier steric environment around the catalytic center, which can influence selectivity and substrate scope.
Can NO-Feng-PDPhMPPr be used in Lewis acid catalysis?
Yes. It is designed to form highly active chiral Lewis acid complexes with various metals and is widely used in asymmetric catalysis.
How should NO-Feng-PDPhMPPr 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 yield and enantioselectivity.