Product Name
NO-Feng-PPhPPi, L-PiPh, 95%
Molecular Formula
C27H36N4O4
Certificate of Analysis (COA)
IUPAC Name
(1R,2S)-1-oxido-1-3-(1R,2S)-1-oxido-2-(phenylcarbamoyl)piperidin-1-ium-1-ylpropyl-N-phenylpiperidin-1-ium-2-carboxamide
InChI Key
SKBHFBKICMHORE-NZWZHHCMSA-N
SMILES
C1CCN@+(C@@H(C1)C(=O)NC2=CC=CC=C2)(CCCN@@+3(CCCCC@H3C(=O)NC4=CC=CC=C4)O-)O-
What is NO-Feng-PPhPPi used for?
NO-Feng-PPhPPi is primarily used as a chiral N,N'-dioxide ligand for asymmetric catalysis and enantioselective synthesis. It is widely employed in chiral metal catalyst systems for stereoselective organic transformations.
What is the alternative name of NO-Feng-PPhPPi?
NO-Feng-PPhPPi is commonly referred to as L-PiPh, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PPhPPi?
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.
What is L-PiPh ligand?
L-PiPh is the abbreviated name of NO-Feng-PPhPPi, a chiral N,N'-dioxide ligand developed for asymmetric catalysis.
Can NO-Feng-PPhPPi improve enantioselectivity?
Yes. Its chiral framework enables efficient stereochemical induction and can provide excellent enantiomeric excess in many asymmetric reactions.
Is NO-Feng-PPhPPi suitable for catalyst development?
Yes. It is widely used in catalyst screening, ligand optimization, asymmetric reaction development, and mechanistic studies involving chiral Lewis acid catalysis.
Which catalytic reactions can benefit from this ligand?
NO-Feng-PPhPPi can be used in a variety of asymmetric transformations, including:
- Asymmetric Michael reactions
- Mannich reactions
- Aldol reactions
- Cycloaddition reactions
- Lewis acid catalysis
- Enantioselective carbon–carbon bond formation
These transformations benefit from the highly organized chiral environment created by the ligand-metal complex.
Which metal catalysts are commonly used with NO-Feng-PPhPPi?
The ligand can coordinate with a variety of Lewis acidic metals, including:
- Sc(III)
- Cu(II)
- Fe(II/III)
- Mg(II)
- Ni(II)
- Yb(III)
- Other rare-earth metal catalysts
These complexes are widely employed in asymmetric synthesis and catalyst development.
Can NO-Feng-PPhPPi 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 high catalytic activity and excellent enantioselectivity.
What are the advantages of NO-Feng-PPhPPi 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
How should NO-Feng-PPhPPi be stored?
The product is typically stored at −20°C under dry, light-protected, and sealed conditions to maintain long-term stability.
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.
What makes L-PiPh different from other Feng ligands?
L-PiPh contains a phenyl-substituted aromatic framework, which can modify the steric and electronic environment around the catalytic center, potentially influencing reaction selectivity and substrate compatibility.
Can NO-Feng-PPhPPi 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.