798339
Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
Synonym(s):
(1S,4S,5R)-5-(naphthalen-1-yl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
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About This Item
Empirical Formula (Hill Notation):
C22H22NO2PS
Molecular Weight:
395.45
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
form
powder
Quality Segment
storage condition
under inert gas
functional group
phosphine, sulfonamide
storage temp.
2-8°C
SMILES string
O=S(N1C[C@@]2([H])[P@](C3=CC=CC4=C3C=CC=C4)C[C@]1([H])C2)(C5=CC=C(C)C=C5)=O
InChI
1S/C22H22NO2PS/c1-16-9-11-20(12-10-16)27(24,25)23-14-19-13-18(23)15-26(19)22-8-4-6-17-5-2-3-7-21(17)22/h2-12,18-19H,13-15H2,1H3/t18-,19-,26?/m0/s1
InChI key
RGHUOMJULXTHPX-OCOBAGFRSA-N
Application
The bicyclic, chiral phosphine was developed by the Kwon Research Group.Its initial applications were for asymmetric [3+2] annulation between allenes and imines as well as the first examples of phosphine-catalyzed asymmetric syntheses of 1,2,3,5-substituted pyrrolines. Along with nucleophilic organocatalysis, the P-chiral phosphines may also find utility in asymmetric transition-metal catalysis.
Other Notes
Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (-)-Pyrrolines
Technology Spotlight- Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline
Aldrichimica Acta Review- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations
Technology Spotlight- Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline
Aldrichimica Acta Review- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations
Signal Word
Warning
Hazard Codes
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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