Cat. No JK1595287_250_MG
J&K Chemical

Product Information

Product Name
NO-Feng-PDiPPRa, L-RaPr2, 95%
Brand Name
J&K
Product Number
1595287
CAS
1005495-74-8
SDS Document
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
44243485
IUPAC Name
(2S,3aS,6aS)-1-3-(2S,3aS,6aS)-2-2,6-di(propan-2-yl)phenylcarbamoyl-1-oxido-3,3a,4,5,6,6a-hexahydro-2H-cyclopentabpyrrol-1-ium-1-ylpropyl-N-2,6-di(propan-2-yl)phenyl-1-oxido-3,3a,4,5,6,6a-hexahydro-2H-cyclopentabpyrrol-1-ium-2-carboxamide
InChI Key
AUXDXJFVTHFWLI-KQALKABTSA-N
SMILES
CC(C)C1=C(C(=CC=C1)C(C)C)NC(=O)C@@H2CC@@H3CCCC@@H3N+2(CCCN+4(C@H5CCCC@H5CC@H4C(=O)NC6=C(C=CC=C6C(C)C)C(C)C)O-)O-

Safety Information

Precautionary Statement
P262
Storage Condition
Store at 0℃

Application

Product Introduction

N,N'-Dioxides (Bis-N-oxide Compounds) are an ideal class of ligands and catalysts for asymmetric synthesis. These chiral N,N'-dioxide compounds overcome the traditional requirement for highly rigid ligand frameworks. Much like a pair of nunchaku, they combine rigidity and flexibility, allowing precise control over how reactants approach and interact during a chemical reaction. By directing the orientation and encounter of reaction partners, these ligands help ensure that chemical bonds are formed in the desired manner, resulting in high catalytic efficiency and excellent enantioselectivity.

Application:

Asymmetric Catalysis:

1、Roskamp–Feng reaction1

2、Electrophilic addition of α-diazoesters to ketones2

3、ring expansion of isatins with α-diazoesters3

4、Baeyer–Villiger oxidation84

5、inverse electron-demand aza-Diels–Alder reaction5

6、reduction reaction6

7、8 + 2 cycloaddition7;

FAQ

What is NO-Feng-PDiPPRa used for?
NO-Feng-PDiPPRa 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-PDiPPRa?
NO-Feng-PDiPPRa is commonly referred to as L-RaPr₂, a member of the Feng chiral ligand family.

 

What type of ligand is NO-Feng-PDiPPRa?
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-PDiPPRa has been successfully applied in a wide range of asymmetric transformations, including:

  • Roskamp–Feng reaction
  • α-Diazoester addition reactions
  • Ring expansion of isatins
  • Baeyer–Villiger oxidation
  • Aza-Diels–Alder reactions
  • Reduction reactions
  • Cycloaddition 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-PDiPPRa?
The ligand can coordinate with multiple 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 used in asymmetric synthesis and catalyst development.

 

Can NO-Feng-PDiPPRa 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 (often described as “nunchaku-like”), enabling precise control of substrate orientation and transition-state organization, leading to high enantioselectivity.

 

What are the advantages of NO-Feng-PDiPPRa compared with conventional ligands?

  • High enantioselectivity
  • Strong metal coordination ability
  • Broad substrate compatibility
  • Excellent catalytic efficiency
  • Tunable steric environment
  • Wide application in asymmetric catalysis

 

What makes L-RaPr₂ different from other Feng ligands?
L-RaPr₂ contains a 2,6-diisopropylphenyl-substituted structural motif, which provides strong steric shielding around the catalytic center, potentially improving selectivity in asymmetric reactions.

 

Can NO-Feng-PDiPPRa be used in Lewis acid catalysis?
Yes. It is designed to form highly active chiral Lewis acid complexes and is widely used in asymmetric catalytic transformations.

 

How should NO-Feng-PDiPPRa be stored?
It is typically recommended to store the compound in a sealed, dry environment at low temperature (0–8°C or below) to maintain stability.

 

Does catalytic performance depend on reaction conditions?
Yes. Parameters such as metal source, solvent, temperature, substrate structure, and catalyst loading significantly affect reaction yield and enantioselectivity.

References

[3 + 2]Cycloadditions of 2,3-Dihydro-1,4-dioxin

Publication Name: Science of Synthesis
Publication Date: 2021

NO-Feng-PDiPPRa, L-RaPr2, 95%

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