Product Name
NO-Feng-PCyPPi, L-PicH, 95%
Molecular Formula
C27H48N4O4
Certificate of Analysis (COA)
IUPAC Name
(2S)-N-cyclohexyl-1-3-(2S)-2-(cyclohexylcarbamoyl)-1-oxidopiperidin-1-ium-1-ylpropyl-1-oxidopiperidin-1-ium-2-carboxamide
InChI Key
PEGGEFQIPSUKDR-RAJFACKRSA-N
SMILES
C1CCC(CC1)NC(=O)C@@H2CCCCN+2(CCCN+3(CCCCC@H3C(=O)NC4CCCCC4)O-)O-
What is NO-Feng-PDMPPi used for?
NO-Feng-PDMPPi 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-PDMPPi?
NO-Feng-PDMPPi is commonly referred to as L-PiMe₂, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PDMPPi?
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-PDMPPi 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 transformations benefit from the highly organized chiral environment generated by the ligand-metal complex.
Which metal catalysts are commonly used with NO-Feng-PDMPPi?
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 utilized in asymmetric synthesis and catalyst development.
Can NO-Feng-PDMPPi be used for pharmaceutical synthesis research?
Yes. Chiral N,N'-dioxide ligands are frequently used 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 of substrate orientation and transition-state organization. This often results in high catalytic activity and excellent enantioselectivity.
What are the advantages of NO-Feng-PDMPPi 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-PiMe₂ different from other Feng ligands?
L-PiMe₂ contains a dimethyl-substituted aromatic framework, which provides a unique steric and electronic environment around the catalytic center. This structural feature may influence substrate scope, catalytic activity, and stereoselectivity compared with other Feng ligand derivatives.
Can NO-Feng-PDMPPi 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-PDMPPi be stored?
The product should be stored in a cool, dry, and well-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.