Product Name
NO-Feng-PDiPPPr, L-PrPr2, 99%
Certificate of Analysis (COA)
IUPAC Name
(1R,2S)-N-2,6-di(propan-2-yl)phenyl-1-3-(1R,2S)-2-2,6-di(propan-2-yl)phenylcarbamoyl-1-oxidopyrrolidin-1-ium-1-ylpropyl-1-oxidopyrrolidin-1-ium-2-carboxamide
InChI Key
GRKRBQGUOZNATH-WXKUUGAPSA-N
SMILES
CC(C)C1=C(C(=CC=C1)C(C)C)NC(=O)C@@H2CCCN@+2(CCCN@@+3(CCCC@H3C(=O)NC4=C(C=CC=C4C(C)C)C(C)C)O-)O-
What is NO-Feng-PDiPPPr used for?
NO-Feng-PDiPPPr is primarily used as a chiral N,N'-dioxide ligand for asymmetric catalysis and enantioselective synthesis. It is widely employed in the construction of chiral metal catalyst systems for stereoselective organic transformations.
What is the alternative name of NO-Feng-PDiPPPr?
NO-Feng-PDiPPPr is commonly referred to as L-PrPr₂ (Feng L₃-PrPr₂), a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PDiPPPr?
It belongs to the Feng Chiral N,N'-Dioxide Ligand Series, a class of privileged ligands recognized for their excellent stereochemical control and broad applicability in asymmetric catalytic reactions.
Which catalytic reactions can benefit from this ligand?
NO-Feng-PDiPPPr has been applied in numerous asymmetric transformations, including:
- Homologation of α-ketoesters and α-diazoesters
- Asymmetric Michael reactions
- Mannich reactions
- Cycloaddition reactions
- Lewis acid catalysis
- Enantioselective carbon–carbon bond formation
- Asymmetric dearomatization reactions
- Enantioselective allylation of ketones
These transformations benefit from the highly organized chiral environment generated by the ligand–metal complex.
Which metal catalysts are commonly used with NO-Feng-PDiPPPr?
The ligand can coordinate with a variety of Lewis acidic metals, including:
- Sc(III)
- Mg(II)
- In(III)
- Cu(II)
- Fe(II/III)
- Ni(II)
- Yb(III)
- Other rare-earth metal catalysts
These metal–ligand complexes are widely used in asymmetric synthesis and catalyst development.
Can NO-Feng-PDiPPPr be used for pharmaceutical synthesis research?
Yes. Chiral N,N'-dioxide ligands are frequently utilized in the synthesis of enantioenriched pharmaceutical intermediates, natural products, and biologically active compounds.
Why are Feng ligands important in asymmetric catalysis?
Feng ligands combine structural rigidity and flexibility within a single framework, enabling precise control over substrate orientation and transition-state organization. This often results in excellent catalytic activity and high enantioselectivity.
What are the advantages of NO-Feng-PDiPPPr compared with conventional chiral ligands?
- High enantioselectivity
- Strong metal coordination ability
- Broad substrate compatibility
- Excellent catalytic efficiency
- Good structural tunability
- Wide applicability in asymmetric transformations
What makes L-PrPr₂ different from other Feng ligands?
L-PrPr₂ is a proline-derived N,N'-dioxide ligand bearing 2,6-diisopropylphenyl substituents. Its unique steric environment can significantly influence catalyst activity, substrate scope, diastereoselectivity, and enantioselectivity compared with other Feng ligand derivatives.
Can NO-Feng-PDiPPPr be used in Lewis acid catalysis?
Yes. It is specifically designed to form highly active chiral Lewis acid complexes with various metal ions and has been widely applied in asymmetric catalytic transformations.
How should NO-Feng-PDiPPPr be stored?
The product is typically stored under dry, sealed, and light-protected conditions. Long-term storage at −20°C is commonly recommended, while commercial specifications may indicate refrigerated storage conditions.
Does catalytic performance depend on reaction conditions?
Yes. Factors such as metal source, solvent, temperature, substrate structure, catalyst loading, and reaction time can significantly influence catalytic activity and enantioselectivity.