Product Name
NO-Feng-PDMPPi, L-PiMe2, 95%
Molecular Formula
C29H40N4O4
Certificate of Analysis (COA)
IUPAC Name
(1R,2S)-N-(2,6-dimethylphenyl)-1-3-(1R,2S)-2-(2,6-dimethylphenyl)carbamoyl-1-oxidopiperidin-1-ium-1-ylpropyl-1-oxidopiperidin-1-ium-2-carboxamide
InChI Key
HLFQNVHPIKHXJE-RLCYBDLISA-N
SMILES
CC1=C(C(=CC=C1)C)NC(=O)C@@H2CCCCN@+2(CCCN@@+3(CCCCC@H3C(=O)NC4=C(C=CC=C4C)C)O-)O-
What is NO-Feng-PCyPPi used for?
NO-Feng-PCyPPi is primarily used as a chiral N,N'-dioxide ligand for asymmetric catalysis and enantioselective synthesis. It is widely employed in the development of chiral metal catalyst systems for stereoselective organic transformations.
What is the alternative name of NO-Feng-PCyPPi?
NO-Feng-PCyPPi is commonly referred to as L-PiCy, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PCyPPi?
It belongs to the Feng Chiral N,N'-Dioxide Ligand Series, a class of privileged ligands known for their excellent stereochemical control and broad applicability in asymmetric catalytic reactions.
Which catalytic reactions can benefit from this ligand?
NO-Feng-PCyPPi has been successfully applied 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 highly organized chiral environment generated by the ligand–metal complex.
Which metal catalysts are commonly used with NO-Feng-PCyPPi?
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 metal–ligand complexes are widely employed in asymmetric synthesis and catalyst development.
Can NO-Feng-PCyPPi 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 molecular 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-PCyPPi 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-PiCy different from other Feng ligands?
L-PiCy contains a cyclohexyl-substituted aromatic framework, which provides a distinctive steric environment around the catalytic center. This structural feature can influence substrate recognition, catalyst activity, and stereoselectivity compared with other Feng ligand derivatives.
Can NO-Feng-PCyPPi 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-PCyPPi be stored?
The product should be stored in a cool, dry, and tightly sealed container, protected from moisture and light. Long-term storage at −20°C is recommended.
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.