Product Name
NO-Feng-PDMPRa, L-RaMe2, 99%
Molecular Formula
C35H48N4O4
Certificate of Analysis (COA)
IUPAC Name
(1S,2S,3aS,6aS)-1-3-(1S,2S,3aS,6aS)-2-(2,6-dimethylphenyl)carbamoyl-1-oxido-3,3a,4,5,6,6a-hexahydro-2H-cyclopentabpyrrol-1-ium-1-ylpropyl-N-(2,6-dimethylphenyl)-1-oxido-3,3a,4,5,6,6a-hexahydro-2H-cyclopentabpyrrol-1-ium-2-carboxamide
InChI Key
OHRCPEXQTDIZCE-UBMXSSLWSA-N
SMILES
CC1=C(C(=CC=C1)C)NC(=O)C@@H2CC@@H3CCCC@@H3N@+2(CCCN@@+4(C@H5CCCC@H5CC@H4C(=O)NC6=C(C=CC=C6C)C)O-)O-
What is NO-Feng-PDMPRa used for?
NO-Feng-PDMPRa is primarily used as a chiral N,N'-dioxide ligand for asymmetric catalysis and enantioselective synthesis. It is widely applied in Lewis acid–catalyzed stereoselective organic transformations.
What is the alternative name of NO-Feng-PDMPRa?
NO-Feng-PDMPRa is commonly referred to as L-RaMe₂, a member of the Feng chiral ligand family.
What type of ligand is NO-Feng-PDMPRa?
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-PDMPRa has been applied 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 C–C bond-forming reactions
These reactions benefit from the well-defined chiral environment formed by the ligand–metal complex.
Which metal catalysts are commonly used with NO-Feng-PDMPRa?
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
Can NO-Feng-PDMPRa be used for pharmaceutical synthesis research?
Yes. It is 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 within a single framework, enabling precise control of substrate orientation and transition-state organization, leading to high enantioselectivity.
What are the advantages of NO-Feng-PDMPRa compared with conventional ligands?
- High enantioselectivity
- Strong metal coordination ability
- Broad substrate compatibility
- Excellent catalytic efficiency
- Tunable steric and electronic properties
- Wide application in asymmetric catalysis
What makes L-RaMe₂ different from other Feng ligands?
L-RaMe₂ contains a dimethyl-substituted aromatic framework, which provides a unique steric environment around the catalytic center and can influence catalytic selectivity and reactivity.
Can NO-Feng-PDMPRa be used in Lewis acid catalysis?
Yes. It is designed to form highly active chiral Lewis acid complexes with various metal ions and is widely used in asymmetric catalysis.
How should NO-Feng-PDMPRa be stored?
It should be stored in a dry, sealed, and light-protected environment, typically at −20°C for long-term stability.
Does catalytic performance depend on reaction conditions?
Yes. Factors such as metal source, solvent, temperature, substrate structure, and catalyst loading strongly influence reaction yield and enantioselectivity.